- Multimetallic catalysed cross-coupling of aryl bromides with aryl triflates
-
The advent of transition-metal catalysed strategies for forming new carbon-carbon bonds has revolutionized the field of organic chemistry, enabling the efficient synthesis of ligands, materials, and biologically active molecules. In cases where a single metal fails to promote a selective or efficient transformation, the synergistic cooperation of two distinct catalysts - multimetallic catalysis - can be used instead. Many important reactions rely on multimetallic catalysis, such as the Wacker oxidation of olefins and the Sonogashira coupling of alkynes with aryl halides, but this approach has largely been limited to the use of metals with distinct reactivities, with only one metal catalyst undergoing oxidative addition. Here, we demonstrate that cooperativity between two group 10 metal catalysts - (bipyridine)nickel and (1,3-bis(diphenylphosphino)propane)palladium - enables a general cross-Ullmann reaction (the cross-coupling of two different aryl electrophiles). Our method couples aryl bromides with aryl triflates directly, eliminating the use of arylmetal reagents and avoiding the challenge of differentiating between multiple carbon-hydrogen bonds that is required for direct arylation methods. Selectivity can be achieved without an excess of either substrate and originates from the orthogonal reactivity of the two catalysts and the relative stability of the two arylmetal intermediates. While (1,3-bis(diphenylphosphino)propane)palladium reacts preferentially with aryl triflates to afford a persistent intermediate, (bipyridine)nickel reacts preferentially with aryl bromides to form a transient, reactive intermediate. Although each catalyst forms less than 5 per cent cross-coupled product in isolation, together they are able to achieve a yield of up to 94 per cent. Our results reveal a new method for the synthesis of biaryls, heteroaryls, and dienes, as well as a general mechanism for the selective transfer of ligands between two metal catalysts. We anticipate that this reaction will simplify the synthesis of pharmaceuticals, many of which are currently made with pre-formed organometallic reagents, and lead to the discovery of new multimetallic reactions.
- Ackerman, Laura K. G.,Lovell, Matthew M.,Weix, Daniel J.
-
-
Read Online
- Phosphine and palladium-free synthesis of aryl and alkenyl boronates: A nano-catalytic approach
-
Superparamagnetic copperferrite nanoparticle is employed as an environmentally benign and efficient catalyst to affect the borylation of aryliodides yielding the corresponding arylboronates at low catalyst loading under mild reaction conditions. This protocol tolerates various substituents present in aryl iodides and also could be extended to beta bromostyrenes in the absence of phosphine and palladium.
- Mohan, Balaji,Kang, Hyuntae,Park, Kang Hyun
-
-
Read Online
- Sequential dehydrogenation-arylation of diisopropylamine-borane complex catalyzed by palladium nanoparticles
-
Palladium nanoparticles have been prepared using different techniques, CO2-assisted microfluidics coflow or thermolysis using ionic liquids. Both techniques displayed interesting activities in dehydrogenation of diisopropylamine-borane complex, and allowed performing a dehydrogenation-arylation sequence with the creation of a carbon-boron bond.
- Guerrand, Hélène D.S.,Marciasini, Ludovic D.,Gendrineau, Thomas,Pascu, Oana,Marre, Samuel,Pinet, Sandra,Vaultier, Michel,Aymonier, Cyril,Pucheault, Mathieu
-
-
Read Online
- Unreactive C-N Bond Activation of Anilines via Photoinduced Aerobic Borylation
-
Unreactive C-N bond activation of anilines was achieved by photoinduced aerobic borylation. A diverse range of tertiary and secondary anilines were converted to aryl boronate esters in moderate to good yields with wide functional group tolerance under simple and ambient photochemical conditions. This transformation achieved the direct and facile C-N bond activation of unreactive anilines, providing a convenient and practical route transforming widely available anilines into useful aryl boronate esters.
- Ji, Shuohan,Qin, Shengxiang,Yin, Chunyu,Luo, Lu,Zhang, Hua
-
supporting information
p. 64 - 68
(2021/12/27)
-
- Merging Iridium-Catalyzed C-H Borylations with Palladium-Catalyzed Cross-Couplings Using Triorganoindium Reagents
-
A versatile and efficient method to prepare borylated arenes furnished with alkyl, alkenyl, alkynyl, aryl, and heteroaryl functional groups is developed by merging Ir-catalyzed C-H borylations (CHB) with a chemoselective palladium-catalyzed cross-coupling of triorganoindium reagents (Sarandeses-Sestelo coupling) with aryl halides bearing a boronic ester substituent. Using triorganoindium cross-coupling reactions to introduce unsaturated moieties enables the synthesis of borylated arenes that would be difficult to access through the direct application of the CHB methodology. The sequential double catalyzed procedure can be also performed in one vessel.
- Jayasundara, Chathurika R. K.,Gil-Negrete, José M.,Montero Bastidas, Jose R.,Chhabra, Arzoo,Martínez, M. Montserrat,Pérez Sestelo, José,Smith, Milton R.,Maleczka, Robert E.
-
p. 751 - 759
(2021/12/27)
-
- Photo-induced thiolate catalytic activation of inert Caryl-hetero bonds for radical borylation
-
Substantial effort is currently being devoted to obtaining photoredox catalysts with high redox power. Yet, it remains challenging to apply the currently established methods to the activation of bonds with high bond dissociation energy and to substrates with high reduction potentials. Herein, we introduce a novel photocatalytic strategy for the activation of inert substituted arenes for aryl borylation by using thiolate as a catalyst. This catalytic system exhibits strong reducing ability and engages non-activated Caryl–F, Caryl–X, Caryl–O, Caryl–N, and Caryl–S bonds in productive radical borylation reactions, thus expanding the available aryl radical precursor scope. Despite its high reducing power, the method has a broad substrate scope and good functional-group tolerance. Spectroscopic investigations and control experiments suggest the formation of a charge-transfer complex as the key step to activate the substrates.
- K?nig, Burkhard,Wang, Hua,Wang, Shun
-
p. 1653 - 1665
(2021/06/17)
-
- Selective C-O Bond Reduction and Borylation of Aryl Ethers Catalyzed by a Rhodium-Aluminum Heterobimetallic Complex
-
We report the catalytic reduction of a C-O bond and the borylation by a rhodium complex bearing an X-Type PAlP pincer ligand. We have revealed the reaction mechanism based on the characterization of the reaction intermediate and deuterium-labeling experiments. Notably, this novel catalytic system shows steric-hindrance-dependent chemoselectivity that is distinct from conventional Ni-based catalysts and suggests a new strategy for selective C-O bond activation by heterobimetallic catalysis.
- Hara, Naofumi,Nakao, Yoshiaki,Saito, Teruhiko,Seki, Rin
-
supporting information
p. 6388 - 6394
(2021/05/31)
-
- Photoinduced Deaminative Borylation of Unreactive Aromatic Amines Enhanced by CO2
-
Herein, direct unreactive C-N borylation of aromatic amines by a photocatalyst was achieved. The C-N borylation of aromatic amines with bis(pinacolato)diboron (B2pin2) proceeded using a pyrene catalyst under light irradiation to afford desired borylated products and aminoborane as a byproduct. The yield of the borylated product improved under a CO2 atmosphere which probably reduced the inhibitory effect of aminoborane. Mechanistic studies suggested that the C-N bond cleavage and C-B bond formation proceeded via a concerted pathway.
- Shiozuka, Akira,Sekine, Kohei,Kuninobu, Yoichiro
-
p. 4774 - 4778
(2021/06/28)
-
- Electrochemical Thiolation and Borylation of Arylazo Sulfones with Thiols and B2pin2
-
An efficient electrochemical synthesis approach of various unsymmetrical thioethers and arylboronates has been developed. Bench stable arylazo sulfones were used as radical precursors for carbon-heteroatom bond formation under electrochemical conditions. Moreover, the scalability of this approach was evaluated by performing the electrochemical thiolation and borylation of arylazo sulfones with thiols and B2pin2 on a gram scale. This protocol not only avoided the use of stoichiometric oxidants, metal catalysts, activating agents and even added bases, but also exhibited favorable functional group tolerance. (Figure presented.).
- Wang, Rongkang,Chen, Fangming,Jiang, Lvqi,Yi, Wenbin
-
supporting information
p. 1904 - 1911
(2021/02/12)
-
- Activation of Aryl Carboxylic Acids by Diboron Reagents towards Nickel-Catalyzed Direct Decarbonylative Borylation
-
The Ni-catalyzed decarbonylative borylation of (hetero)aryl carboxylic acids with B2cat2 has been achieved without recourse to any additives. This Ni-catalyzed method exhibits a broad substrate scope covering poorly reactive non-ortho-substituted (hetero)aryl carboxylic acids, and tolerates diverse functional groups including some of the groups active to Ni0 catalysts. The key to achieve this decarbonylative borylation reaction is the choice of B2cat2 as a coupling partner that not only acts as a borylating reagent, but also chemoselectively activates aryl carboxylic acids towards oxidative addition of their C(acyl)?O bond to Ni0 catalyst via the formation of acyloxyboron compounds. A combination of experimental and computational studies reveals a detailed plausible mechanism for this reaction system, which involves a hitherto unknown concerted decarbonylation and reductive elimination step that generates the aryl boronic ester product. This mode of boron-promoted carboxylic acid activation is also applicable to other types of reactions.
- Deng, Xi,Guo, Jiandong,Su, Weiping,Wang, Xiaotai,Zhang, Xiaofeng
-
p. 24510 - 24518
(2021/08/12)
-
- Zinc Complexes with an Ethylene-Bridged Bis(β-diketiminate) Ligand: Syntheses, Structures, and Applications as Catalysts in the Borylation of Aryl Iodides
-
A dinucleating bis(β-diketiminate) ligand with a flexible bridge has been employed to synthesize zinc complexes. The ligand, abbreviated H2L (H2L = N-(4-((2-((4-((2,6-diisopropylphenyl)imino)pent-2-en-2-yl)amino)ethyl)imino)pent-2-en-2-yl)-2,6-diisopropylaniline), was deprotonated with ZnEt2 to afford [LZn2Et2] (1). Reactions of 1 with 2 equiv of BnOH and nBuOH, respectively, gave access to [LZn2(OBn)2]·C6H14 (2·C6H14) and [LZn2(OnBu)2] (3). Treatment of 1 with 2 equiv of I2 in THF produced [LZn2I2(THF)2]·2THF (4·2THF). X-ray single-crystal diffraction analyses revealed that they are all heteroleptic bimetallic compounds with two metal centers being chelated by one ligand set. The structurally similar compounds 1 and 4·2THF possess approximate C2 symmetry, with two β-diketiminate units being arrayed in head-to-tail antiparallel mode. Thus, the molecular structures of 1 and 4·2THF exhibit a seesaw-like topology. The structures of 2·C6H14 and 3 are almost identical, in which two zinc atoms are shared by two ZnN2C3 six-membered rings, two Zn2ON2C2 seven-membered rings, and one Zn2O2 four-membered ring. Therefore, the metal cores of 2·C6H14 and 3 display a crownlike topology. All complexes are catalytically active for the borylation of aryl iodides with B2Pin2 (B2Pin2 = 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bis(1,3,2-dioxaborolane). Complex 1 shows higher activity in comparison to 2, 3, and 4·2THF. The borylation reactions catalyzed by 1 could proceed under mild conditions and can be applied to a series of substrates with high functional group generality. This methodology thus represents a novel use of β-diketiminate zinc complexes for C-I borylation.
- Li, Yafei,Dang, Yan,Li, Dawei,Pan, Huifen,Zhang, Liang,Wang, Li,Cao, Zhu,Li, Yahong
-
supporting information
p. 482 - 489
(2021/03/01)
-
- Engaging Ag(0) single atoms in silver(I) salts-mediated C-B and C-S coupling under visible light irradiation
-
Silver(I) salts were found active in the borylation and sulfenylation of aryl iodides under visible light irradiation. The optimized borylation protocol using AgF did not need any additive, operated under very mild conditions, and well tolerated a broad scope of substrates and boron sources. Formation of Ag(0) single atoms (AgSAs) during the borylation reactions was examined using high-angle annular dark field aberration-corrected scanning transmission electron microscope (HAADF AC-STEM) and electron paramagnetic resonance (EPR). The activities of the silver(I) salts were affected by the anions and could be associated with their abilities in formation of AgSAs during the reactions. Kinetic studies showed that the deiodination rate was linearly correlated with the loading of AgSAs, and hence AgSAs were the true catalytic centers for the 1e?-reduction of the C-I moieties. The oxidation state of AgSAs kept 0 in both the resting and the working states. A “work-in-tandem” mechanism involving AgSAs as the catalytic centers and AgNPs as the light absorber to achieve the borylation of aryl iodides under visible light irradiation is proposed. The current approach not only provides an alternative system for borylation and sulfenylation of aryl iodides, but also reveals a new activity of silver(I) salts involving AgSAs under visible light irradiation.
- Cui, Enxin,Guo, Lirong,Li, Haibin,Qiao, Dan,Tung, Chen-Ho,Wang, Yifeng
-
p. 255 - 263
(2021/09/06)
-
- End-Functionalization of Diarylethene for Opto-Electronic Switching with High Fatigue Resistance
-
A molecular and synthetic approach to strengthen the switching performance of diarylethene (DAE)-based organic transistors is proposed. By tuning the length of alkyl side chains of the biphenyl unit attached to 1,2-bis(5-biphenyl-2-methylthien-3-yl)perfluorocyclopentene (DAE), we show that the molecular environment for reversible photoisomerization of DAEs can be optimized. Four different DAEs are synthesized with different alkyl chains (DAE_C0, DAE_C1, DAE_C6, and DAE_C10), and ITIC is chosen to construct a semiconductor matrix to maximize the quantum yield of photoconversion considering the complementary absorption range of both materials. From photophysical, structural, and morphological analyses, the longer alkyl chains inhibit intermolecular aggregation between DAEs and allow more hydrophobic surface properties of DAEs, thus improving molecular miscibility with ITIC. The improved molecular compatibility of DAEs with ITIC makes the overall bulk heterojunction film amorphous, allowing more free volume for reversible photoisomerization. Consequently, DAE_C6 exhibits the maximum quantum yield for both photocyclization and photocycloreversion, enabling high light-controlled on/off ratios in photoswitchable transistors. Furthermore, the exceptionally high DAE_C6 quantum yield enables robust fatigue resistance under repeated photoswitching with only a 30% decrease in the on/off ratio after 100 cycles. Overall, this work shows that not only the energy level but also the molecular compatibility can endow significant switching performances for molecular switches.
- Hassan, Syed Zahid,Yu, Seong Hoon,So, Chan,Moon, Dohyun,Chung, Dae Sung
-
p. 403 - 412
(2021/01/13)
-
- Cross-Coupling through Ag(I)/Ag(III) Redox Manifold
-
In ample variety of transformations, the presence of silver as an additive or co-catalyst is believed to be innocuous for the efficiency of the operating metal catalyst. Even though Ag additives are required often as coupling partners, oxidants or halide scavengers, its role as a catalytically competent species is widely neglected in cross-coupling reactions. Most likely, this is due to the erroneously assumed incapacity of Ag to undergo 2e? redox steps. Definite proof is herein provided for the required elementary steps to accomplish the oxidative trifluoromethylation of arenes through AgI/AgIII redox catalysis (i. e. CEL coupling), namely: i) easy AgI/AgIII 2e? oxidation mediated by air; ii) bpy/phen ligation to AgIII; iii) boron-to-AgIII aryl transfer; and iv) ulterior reductive elimination of benzotrifluorides from an [aryl-AgIII-CF3] fragment. More precisely, an ultimate entry and full characterization of organosilver(III) compounds [K]+[AgIII(CF3)4]? (K-1), [(bpy)AgIII(CF3)3] (2) and [(phen)AgIII(CF3)3] (3), is described. The utility of 3 in cross-coupling has been showcased unambiguously, and a large variety of arylboron compounds was trifluoromethylated via [AgIII(aryl)(CF3)3]? intermediates. This work breaks with old stereotypes and misconceptions regarding the inability of Ag to undergo cross-coupling by itself.
- Demonti, Luca,Mézailles, Nicolas,Nebra, Noel,Saffon-Merceron, Nathalie
-
supporting information
p. 15396 - 15405
(2021/10/12)
-
- Preparation method of aryl borate catalyzed by cesium neovalerate
-
The preparation method comprises the following steps: dissolving a compound of formula (I) and a diboron compound in an organic solvent, then adding an organic solvent dissolved with cesium neovalerate, palladium acetate and triphenylphosphine, and carrying out reaction to obtain aryl boronic acid ester. In the formula (I) R1. R2, R3, R4 and R5 are each independently selected from H, C. 1 - C10 Alkyl group, C2 - C10 Alkenyl, C2 - C10 Alkynyl group, C1 - C10 Alkoxy, hydroxy, hydroxy-substituted C1 - C10 Alkyl, phenyl, C1 - C10 Alkylamino. X Is selected from F, Cl, Br, i. The preparation method has the advantages of low production cost, high product yield, high purity, simple operation and suitability for industrial mass production.
- -
-
Paragraph 0030-0033; 0066-0067
(2021/09/22)
-
- Anthryl dark blue light material with biphenyl modified carbazole group, preparation and application thereof
-
The invention belongs to the technical field of blue light electroluminescent materials, and discloses an anthryl dark blue light material with a biphenyl modified carbazole group, preparation and application thereof, wherein the structural formula of the anthryl dark blue light material with the biphenyl modified carbazole group is as shown in formula I, R1 and R2 are the same or different, R1 and R2 are independently biphenyl groups or H, and R1 and R2 are not H at the same time. The invention also discloses a preparation method of the anthryl dark blue light material with the biphenyl modified carbazole group. According to the invention, the anthryl dark blue light material with the biphenyl modified carbazole group has the characteristics of good thermal stability, thin film morphology stability, easiness in synthesis and purification and the like; and the anthracene blue light material with the biphenyl modified carbazole group is used for preparing organic electroluminescent devices, and is particularly used as a main body material for preparing high-efficiency and low-efficiency roll-off organic electroluminescent devices.
- -
-
Paragraph 0067; 0071-0073
(2021/07/14)
-
- SOLVENT-FREE CROSS-COUPLING REACTION, AND PRODUCTION METHOD USING SAID REACTION
-
Disclosed is a cross-coupling reaction method which forms a chemical bond selected from C—N, C—B, C—C, C—O and C—S bonds, the method comprising: preparing an aromatic compound (1) having a leaving group;preparing a compound (2) capable of undergoing a cross-coupling reaction selected from an aromatic amino compound (2-1), a diboronic acid ester or the like (2-2), an aromatic boronic acid or the like (2-3), an aromatic compound (2-4) having a hydroxyl group and an aromatic compound (2-5) having a thiol group; andperforming a cross-coupling reaction of the compound (1) with the compound (2) in the presence of a palladium catalyst, a base and a compound (4) having a carbon-carbon double bond or a carbon-carbon triple bond, in the absence of a solvent.
- -
-
Paragraph 0330-0331
(2021/12/30)
-
- Evaluation of the role of graphene-based Cu(i) catalysts in borylation reactions
-
Carbon-supported catalysts have been considered as macromolecular ligands which modulate the activity of the metallic catalytic center. Understanding the properties and the factors that control the interactions between the metal and support allows a fine tuning of the catalyzed processes. Although huge effort has been devoted to comprehending binding energies and charge transfer for single atom noble metals, the interaction of graphenic surfaces with cheap and versatile Cu(i) salts has been scarcely studied. A methodical experimental and theoretical analysis of different carbon-based Cu(i) materials in the context of the development of an efficient, general, scalable, and sustainable borylation reaction of aliphatic and aromatic halides has been performed. We have also examined the effect of microwave (MW) radiation in the preparation of these type of materials using sustainable graphite nanoplatelets (GNP) as a support. A detailed analysis of all the possible species in solution revealed that the catalysis is mainly due to an interesting synergetic Cu2O/graphene performance, which has been corroborated by an extensive theoretical study. We demonstrated through DFT calculations at a high level of theory that graphene enhances the reactivity of the metal in Cu2O against the halide derivative favoring a radical departure from the halogen. Moreover, this material is able to stabilize radical intermediates providing unexpected pathways not observed using homogeneous Cu(i) catalysed reactions. Finally, we proved that other common carbon-based supports like carbon black, graphene oxide and reduced graphene oxide provided poorer results in the borylation process.
- Cid, M. B.,Díaz, Cristina,Franco, Mario,Lamsabhi, Al Mokhtar,Sainz, Raquel,Tortosa, Mariola
-
p. 3501 - 3513
(2021/06/06)
-
- Carbon-carbon bond activation by B(OMe)3/B2pin2-mediated fragmentation borylation
-
Selective carbon-carbon bond activation is important in chemical industry and fundamental organic synthesis, but remains challenging. In this study, non-polar unstrained Csp2-Csp3 and Csp2-Csp2 bond activation was achieved by B(OMe)3/B2pin2-mediated fragmentation borylation. Various indole derivatives underwent C2-regioselective C-C bond activation to afford two C-B bonds under transition-metal-free conditions. Preliminary mechanistic investigations suggested that C-B bond formation and C-C bond cleavage probably occurred in a concerted process. This new reaction mode will stimulate the development of reactions based on inert C-C bond activation. This journal is
- Chen, Quan,Jiang, Jiachen,Wang, Li,Wu, Aizhen,Yin, Youzhi,Zhang, Hua,Zhang, Ke,Zhao, Mengzhen,Zhong, Qi,Zou, Youliang
-
p. 15104 - 15109
(2021/12/09)
-
- 1,2-Arylboration of aliphatic alkenes by cooperative palladium/copper catalysis
-
A method for the 1,2-arylboration of aliphatic alkenes to afford alkylboronic esters by cooperative palladium/copper catalysis was developed. The reaction proceeds in a highly regioselective manner, and various functional groups such as silyl ether, alkoxycarbonyl, and cyano groups are tolerated under the applied reaction conditions.
- Semba, Kazuhiko,Ohtagaki, Yasuhiro,Nakao, Yoshiaki
-
supporting information
(2021/04/27)
-
- Unveiling Extreme Photoreduction Potentials of Donor-Acceptor Cyanoarenes to Access Aryl Radicals from Aryl Chlorides
-
Since the seminal work of Zhang in 2016, donor-acceptor cyanoarene-based fluorophores, such as 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN), have been widely applied in photoredox catalysis and used as excellent metal-free alternatives to noble metal Ir- and Ru-based photocatalysts. However, all the reported photoredox reactions involving this chromophore family are based on harnessing the energy from a single visible light photon, with a limited range of redox potentials from -1.92 to +1.79 V vs SCE. Here, we document the unprecedented discovery that this family of fluorophores can undergo consecutive photoinduced electron transfer (ConPET) to achieve very high reduction potentials. One of the newly synthesized catalysts, 2,4,5-tri(9H-carbazol-9-yl)-6-(ethyl(phenyl)amino)isophthalonitrile (3CzEPAIPN), possesses a long-lived (12.95 ns) excited radical anion form, 3CzEPAIPN?-*, which can be used to activate reductively recalcitrant aryl chlorides (Ered ≈ -1.9 to -2.9 V vs SCE) under mild conditions. The resultant aryl radicals can be engaged in synthetically valuable aromatic C-B, C-P, and C-C bond formation to furnish arylboronates, arylphosphonium salts, arylphosphonates, and spirocyclic cyclohexadienes.
- Cao, Jilei,Tang, Xinxin,Toh, Ren Wei,Wang, Han,Wu, Jie,Wu, Xiangyang,Xu, Jinhui,Yang, Xiaona,Yeow, Edwin K. L.,Zhou, Rong
-
supporting information
p. 13266 - 13273
(2021/09/07)
-
- Oxazole or thiazole compound and organic electroluminescent device thereof
-
The invention provides an oxazole or thiazole compound and an organic electroluminescent device thereof. Belong to organic electroluminescence technical field. The oxazole or thiazole compound provided by the invention has a proper HOMO energy level, can
- -
-
Paragraph 0123-0124; 0130-0131; 0153-0155
(2021/11/27)
-
- Nickel-Catalyzed Ipso-Borylation of Silyloxyarenes via C-O Bond Activation
-
The conversion of silyloxyarenes to boronic acid pinacol esters via nickel catalysis is described. In contrast to other borylation protocols of inert C-O bonds, the method is competent in activating the carbon-oxygen bond of silyloxyarenes in isolated aromatic systems lacking a directing group. The catalytic functionalization of benzyl silyl ethers was also achieved under these conditions. Sequential cross-coupling reactions were achieved by leveraging the orthogonal reactivity of silyloxyarenes, which could then be functionalized subsequently.
- Pein, Wesley L.,Wiensch, Eric M.,Montgomery, John
-
supporting information
(2021/06/28)
-
- Para-selective borylation of monosubstituted benzenes using a transient mediator
-
Herein, we conceptualized a transient mediator approach that has the capability of para-selective C-H functionalization of monosubstituted aromatics. This approach is enabled by in situ generation of a versatile sulfonium salt via highly electrophilic phenoxathiine or thianthrene dication intermediate which can be readily generated from its sulfoxide with trifluoromethanesulfonic anhydride. Preliminary mechanistic study implied that the remarkable para selectivity might be related to the incredible electrophilicity of thianthrene dication intermediate. The versatility of this approach was demonstrated via para-borylation of various monosubstituted simple aromatics combining the sulfonium salt formation with further photocatalyzed transformation.
- Wu, Jie,Wang, Zengwei,Chen, Xiao-Yue,Wu, Yichen,Wang, Daoming,Peng, Qian,Wang, Peng
-
p. 336 - 340
(2019/12/09)
-
- Visible-Light-Induced Ni-Catalyzed Radical Borylation of Chloroarenes
-
A highly selective and general photoinduced C-Cl borylation protocol that employs [Ni(IMes)2] (IMes = 1,3-dimesitylimidazoline-2-ylidene) for the radical borylation of chloroarenes is reported. This photoinduced system operates with visible light (400 nm) and achieves borylation of a wide range of chloroarenes with B2pin2 at room temperature in excellent yields and with high selectivity, thereby demonstrating its broad utility and functional group tolerance. Mechanistic investigations suggest that the borylation reactions proceed via a radical process. EPR studies demonstrate that [Ni(IMes)2] undergoes very fast chlorine atom abstraction from aryl chlorides to give [NiI(IMes)2Cl] and aryl radicals. Control experiments indicate that light promotes the reaction of [NiI(IMes)2Cl] with aryl chlorides generating additional aryl radicals and [NiII(IMes)2Cl2]. The aryl radicals react with an anionic sp2-sp3 diborane [B2pin2(OMe)]- formed from B2pin2 and KOMe to yield the corresponding borylation product and the [Bpin(OMe)]?- radical anion, which reduces [NiII(IMes)2Cl2] under irradiation to regenerate [NiI(IMes)2Cl] and [Ni(IMes)2] for the next catalytic cycle.
- Tian, Ya-Ming,Guo, Xiao-Ning,Krummenacher, Ivo,Wu, Zhu,Nitsch, J?rn,Braunschweig, Holger,Radius, Udo,Marder, Todd B.
-
supporting information
p. 18231 - 18242
(2020/11/02)
-
- A synthetic approach to dimetalated arenes using flow microreactors and the switchable application to chemoselective cross-coupling reactions
-
In spite of their potential utility, the chemistry of dimetalated arenes is still in its infancy because they are extremely difficult to synthesize. We report a novel method of synthesizing arenes bearing a boryl group and a metallic substituent, such as boryl, silyl, stannyl, or zincyl groups, in an integrated flow microreactor based on the generation and reactions of aryllithiums bearing a trialkyl borate moiety. The bimetallic arenes showed a remarkable chemoselectivity in palladium-catalyzed cross-coupling reactions. The selectivity was switched by the selection of the metal species that constitutes the dimetalated arenes as well as appropriate catalysts.
- Nagaki, Aiichiro,Ashikari, Yosuke,Kawaguchi, Tomoko,Mandai, Kyoko,Aizawa, Yoko
-
supporting information
p. 17039 - 17047
(2020/11/10)
-
- Undirected ortho-selectivity in C–H borylation of arenes catalyzed by NHC platinum(0) complexes
-
Borylation of arenes with bis(pinacolato)diboron catalyzed by sterically encumbered NHC platinum complexes proceeds predominantly at ortho-position even in the absence of a directing group (o: m: p ratio up to 10: 3: 1). The similar borylation with pinacolborane would proceed less selectively.
- Rzhevskiy, Sergey A.,Topchiy, Maxim A.,Golenko, Yulia D.,Gribanov, Pavel S.,Sterligov, Grigorii K.,Kirilenko, Nikita Yu.,Ageshina, Alexandra A.,Bermeshev, Maxim V.,Nechaev, Mikhail S.,Asachenko, Andrey F.
-
p. 569 - 571
(2020/10/09)
-
- Transformations of Aryl Ketones via Ligand-Promoted C?C Bond Activation
-
The coupling of aromatic electrophiles (aryl halides, aryl ethers, aryl acids, aryl nitriles etc.) with nucleophiles is a core methodology for the synthesis of aryl compounds. Transformations of aryl ketones in an analogous manner via carbon–carbon bond activation could greatly expand the toolbox for the synthesis of aryl compounds due to the abundance of aryl ketones. An exploratory study of this approach is typically based on carbon–carbon cleavage triggered by ring-strain release and chelation assistance, and the products are also limited to a specific structural motif. Here we report a ligand-promoted β-carbon elimination strategy to activate the carbon–carbon bonds, which results in a range of transformations of aryl ketones, leading to useful aryl borates, and also to biaryls, aryl nitriles, and aryl alkenes. The use of a pyridine-oxazoline ligand is crucial for this catalytic transformation. A gram-scale borylation reaction of an aryl ketone via a simple one-pot operation is reported. The potential utility of this strategy is also demonstrated by the late-stage diversification of drug molecules probenecid, adapalene, and desoxyestrone, the fragrance tonalid as well as the natural product apocynin.
- Dai, Hui-Xiong,Li, Hanyuan,Li, Ling-Jun,Liu, Qi-Sheng,Ma, Biao,Wang, Mei-Ling,Wang, Xing,Wang, Zhen-Yu,Xu, Hui
-
p. 14388 - 14393
(2020/07/06)
-
- Development and Mechanistic Studies of Iron-Catalyzed Construction of Csp2-B Bonds via C-O Bond Activation
-
Herein we describe an iron-catalyzed borylation of alkenyl and aryl carbamates through the activation of a C-O bond. This protocol exhibits high efficiency, a broad substrate scope, and the late-stage borylation of biorelevant compounds, thus providing potential applications in medicinal chemistry. Moreover, this method enables orthogonal transformations of phenol derivatives and also offers good opportunities for the synthesis of multisubstituted arenes. Preliminary mechanistic studies suggest that a FeII/FeIII catalytic cycle via a radical pathway might be involved in the reaction.
- Geng, Shasha,Zhang, Juan,Chen, Shuo,Liu, Zhengli,Zeng, Xiaoqin,He, Yun,Feng, Zhang
-
supporting information
p. 5582 - 5588
(2020/07/08)
-
- Hydride Transfer Enables the Nickel-Catalyzed ipso-Borylation and Silylation of Aldehydes
-
Nickel-catalyzed ipso-borylations and silylations of aldehydes are described for the first time. The new functional-group interconversion protocol is characterized by its scalability, functional-group tolerance and wide substrate scope, including examples of late-stage functionalization of complex molecules. The key for the successful reaction outcome is the use of a ketone as a hydride acceptor that intercepts the nickel hydride to undergo a reductive pathway, thus allowing formation of the desired C?B and C?Si bonds.
- Srimontree, Watchara,Guo, Lin,Rueping, Magnus
-
supporting information
p. 423 - 427
(2019/12/27)
-
- Visible- And UV-Light-Induced Decarboxylative Radical Reactions of Benzoic Acids Using Organic Photoredox Catalysts
-
Photoinduced decarboxylative radical reactions of benzoic acids with electron-deficient alkenes, diborane, and acetonitrile under organic photoredox catalysis conditions and mild heating afforded adducts, arylboronate esters, and the reduction product, respectively. The reaction is thought to involve single-electron transfer promoted the generation of aryl radicals via decarboxylation. A diverse range of benzoic acids were found to be suitable substrates for this photoreaction. Only our two-molecule organic photoredox system can work well for the direct photoinduced decarboxylation of benzoic acids.
- Kubosaki, Suzuka,Takeuchi, Haruka,Iwata, Yutaka,Tanaka, Yosuke,Osaka, Kazuyuki,Yamawaki, Mugen,Morita, Toshio,Yoshimi, Yasuharu
-
p. 5362 - 5369
(2020/05/19)
-
- Iron-Catalyzed Borylation of Aryl Ethers via Cleavage of C-O Bonds
-
Herein, we report the iron-catalyzed borylation of aryl ethers and aryl amines via cleavage of C-O and C-N bonds. This protocol does not require the use of Grignard reagents and displays a broad substrate scope, which allows the late-stage borylation. It also provides facile access to multisubstituted arenes through C-H functionalization using 2-pyridyloxy as the directing group.
- Zeng, Xiaoqin,Zhang, Yuxuan,Liu, Zhengli,Geng, Shasha,He, Yun,Feng, Zhang
-
p. 2950 - 2955
(2020/04/15)
-
- Organic compound based on azabenzene and anthone structure and application thereof in OLED
-
The compound of the present invention also has a deep OLED energy level and a high electron mobility, which can effectively block holes or energy from being transferred from the light emitting layer to the electron layer side, to improve the recombination
- -
-
Paragraph 0198; 0240; 0241
(2020/03/23)
-
- Luminescent tungsten(vi) complexes as photocatalysts for light-driven C-C and C-B bond formation reactions
-
The realization of photocatalysis for practical synthetic application hinges on the development of inexpensive photocatalysts which can be prepared on a large scale. Herein an air-stable, visible-light-absorbing photoluminescent tungsten(vi) complex which can be conveniently prepared at the gram-scale is described. This complex could catalyse photochemical organic transformation reactions including borylation of aryl halides, such as aryl chloride, reductive coupling of benzyl bromides for C-C bond formation, reductive coupling of phenacyl bromides, and decarboxylative coupling of redox-active esters of alkyl carboxylic acid with high product yields and broad functional group tolerance.
- Chan, Kaai-Tung,Che, Chi-Ming,Du, Lili,Liu, Yungen,Phillips, David Lee,To, Wai-Pong,Tong, Glenna So Ming,Wu, Liang-Liang,Yu, Daohong
-
p. 6370 - 6382
(2020/07/15)
-
- Visible Light-Induced Borylation of C-O, C-N, and C-X Bonds
-
Boronic acids are centrally important functional motifs and synthetic precursors. Visible light-induced borylation may provide access to structurally diverse boronates, but a broadly efficient photocatalytic borylation method that can effect borylation of a wide range of substrates, including strong C-O bonds, remains elusive. Herein, we report a general, metal-free visible light-induced photocatalytic borylation platform that enables borylation of electron-rich derivatives of phenols and anilines, chloroarenes, as well as other haloarenes. The reaction exhibits excellent functional group tolerance, as demonstrated by the borylation of a range of structurally complex substrates. Remarkably, the reaction is catalyzed by phenothiazine, a simple organic photocatalyst with MW 200 that mediates the previously unachievable visible light-induced single electron reduction of phenol derivatives with reduction potentials as negative as approximately - 3 V versus SCE by a proton-coupled electron transfer mechanism. Mechanistic studies point to the crucial role of the photocatalyst-base interaction.
- Arman, Hadi D.,Dang, Hang. T.,Haug, Graham C.,He, Ru,Jin, Shengfei,Larionov, Oleg V.,Nguyen, Viet D.,Nguyen, Vu T.,Schanze, Kirk S.
-
supporting information
(2020/02/04)
-
- Visible-light-mediated borylation of aryl and alkyl halides with a palladium complex
-
Palladium catalyzed visible-light-mediated borylation of inactivated aryl and alkyl halides is reported; the method provided high yields and excellent functional group compatibility. Furthermore, arylsilicates were synthesized selectively using dimethylphenylsilyl boronic ester via changing the reaction conditions. Finally, the possible reaction mechanism is determined through fluorescence quenching and turn on/off experiments.
- Zhao, Jia-Hui,Zhou, Zhao-Zhao,Zhang, Yue,Su, Xuan,Chen, Xi-Meng,Liang, Yong-Min
-
supporting information
p. 4390 - 4394
(2020/10/20)
-
- Reductive Electrophotocatalysis: Merging Electricity and Light to Achieve Extreme Reduction Potentials
-
We describe a new electrophotocatalytic strategy that harnesses the power of light and electricity to generate an excited radical anion with a reducing potential of -3.2 V vs SCE, which can be used to activate substrates with very high reduction potentials (Ered ≈ -1.9 to -2.9 V). The resultant aryl radicals can be engaged in various synthetically useful transformations to furnish arylboronate, arylstannane, and biaryl products.
- Kim, Hyunwoo,Kim, Hyungjun,Lambert, Tristan H.,Lin, Song
-
supporting information
p. 2087 - 2092
(2020/02/04)
-
- Organic compound based on azabenzene and dicarboximide derivative and application of organic compound
-
The invention discloses an organic compound based on azabenzene and a dicarboximide derivative and application of the organic compound, belonging to the technical field of semiconductors. The structure of the compound provided by the invention is shown as
- -
-
Paragraph 0062; 0066-0068; 0069-0071
(2020/09/09)
-
- Visible-Light-Photosensitized Aryl and Alkyl Decarboxylative Functionalization Reactions
-
Despite significant progress in aliphatic decarboxylation, an efficient and general protocol for radical aromatic decarboxylation has lagged far behind. Herein, we describe a general strategy for rapid access to both aryl and alkyl radicals by photosensitized decarboxylation of the corresponding carboxylic acids esters followed by their successive use in divergent carbon–heteroatom and carbon–carbon bond-forming reactions. Identification of a suitable activator for carboxylic acids is the key to bypass a competing single-electron-transfer mechanism and “switch on” an energy-transfer-mediated homolysis of unsymmetrical σ-bonds for a concerted fragmentation/decarboxylation process.
- Patra, Tuhin,Mukherjee, Satobhisha,Ma, Jiajia,Strieth-Kalthoff, Felix,Glorius, Frank
-
supporting information
p. 10514 - 10520
(2019/07/12)
-
- Cleavage of C(aryl)?CH3 Bonds in the Absence of Directing Groups under Transition Metal Free Conditions
-
Organic chemists now can construct carbon–carbon σ-bonds selectively and sequentially, whereas methods for the selective cleavage of carbon–carbon σ-bonds, especially for unreactive hydrocarbons, remain limited. Activation by ring strain, directing groups, or in the presence of a carbonyl or a cyano group is usually required. In this work, by using a sequential strategy site-selective cleavage and borylation of C(aryl)?CH3 bonds has been developed under directing group free and transition metal free conditions. Methyl groups of various arenes are selectively cleaved and replaced by boryl groups. Mechanistic analysis suggests that it proceeds by a sequential intermolecular oxidation and coupling of a transient aryl radical, generated by radical decarboxylation, involving a pyridine-stabilized persistent boryl radical.
- Dai, Peng-Fei,Ning, Xiao-Shan,Wang, Hua,Cui, Xian-Chao,Liu, Jie,Qu, Jian-Ping,Kang, Yan-Biao
-
supporting information
p. 5392 - 5395
(2019/03/29)
-
- Base-Mediated Defluorosilylation of C(sp2)?F and C(sp3)?F Bonds
-
The ability to selectively forge C–heteroatom bonds by C?F scission is typically accomplished by metal catalysts, specialized ligands and/or harsh reaction conditions. Described herein is a base-mediated defluorosilylation of unactivated C(sp2)?F and C(sp3)?F bonds that obviates the need for metal catalysts. This protocol is characterized by its simplicity, mild reaction conditions, and wide scope, even within the context of late-stage functionalization, constituting a complementary approach to existing C?Si bond-forming protocols.
- Liu, Xiang-Wei,Zarate, Cayetana,Martin, Ruben
-
supporting information
p. 2064 - 2068
(2019/01/25)
-
- Visible light-promoted formation of C-B and C-S bonds under metal- A nd photocatalyst-free conditions
-
A green, efficient, photoinduced synthesis of arylboronic esters and aryl sulfides has been developed. Bench stable arylazo sulfones were used as radical precursors for a photocatalyst- A nd additive-free carbon-heteroatom bond formation under visible light. The protocols are applicable to a wide range of substrates, providing products in good yields.
- Blank, Lena,Fagnoni, Maurizio,Protti, Stefano,Rueping, Magnus
-
p. 1243 - 1252
(2019/02/26)
-
- Mechanism and Scope of Nickel-Catalyzed Decarbonylative Borylation of Carboxylic Acid Fluorides
-
This Article describes the development of a base-free, nickel-catalyzed decarbonylative coupling of carboxylic acid fluorides with diboron reagents to selectively afford aryl boronate ester products. Detailed studies were conducted to assess the relative rates of direct transmetalation between aryl boronate esters and diboron reagents and a bisphosphine nickel(aryl)(fluoride) intermediate. These investigations revealed that diboron reagents undergo transmetalation with this Ni(aryl)(fluoride) intermediate at rates significantly faster than their aryl boronate ester congeners. Furthermore, the reactivity of both boron reagents toward transmetalation is enhanced with increasing electrophilicity of the boron center. These mechanistic insights were leveraged to develop a catalytic decarbonylative borylation of acid fluorides that proved applicable to a variety of (hetero)aryl carboxylic acid fluorides as well as diverse diboron reagents. The acid fluorides can be generated in situ directly from carboxylic acids. Furthermore, the mechanistic studies directed the identification of various air-stable Ni pre-catalysts for this transformation.
- Malapit, Christian A.,Bour, James R.,Laursen, Simon R.,Sanford, Melanie S.
-
supporting information
p. 17322 - 17330
(2019/11/03)
-
- Competing dehalogenation versus borylation of aryl iodides and bromides under transition-metal-free basic conditions
-
In this work, selectivity-controllable base-promoted transition-metal-free borylation and dehalogenation of aryl halides are described. Under the conditions of borylation, the dehalogenation which emerges as a competitive side reaction has been well-controlled by carefully controlling the borylation conditions. On the other hand, the dehalogenation using benzaldehyde as a hydrogen source has also been accomplished. The applications of direct radical borylation and dehalogenation of aryl halides demonstrate their synthetic practicability in pharmaceutical-oriented organic synthesis. Based on the experimental evidences, the tBuOK/1,10-Phen-triggered radical nature of both competitive reactions has been revealed.
- Niu, Yi-Jie,Sui, Guo-Hui,Zheng, Hong-Xing,Shan, Xiang-Huan,Tie, Lin,Fu, Jia-Le,Qu, Jian-Ping,Kang, Yan-Biao
-
p. 10805 - 10813
(2019/09/30)
-
- Nickel-Catalyzed C(sp2)-H Borylation of Arenes
-
In this study, C(sp2)-H borylation of arenes was accomplished by a nickel catalyst, resulting in good yield. Alkyl and alkoxy arenes were successfully functionalized, affording C(sp2)-H borylated compounds. It was unraveled that the well-defined abnormal N-heterocyclic carbene based Ni(II) complex breaks into Ni nanoparticles (Ni-NPs), which act as catalytically active species. A series of controlled reactions under stoichiometric conditions along with spectroscopic studies and single-crystal X-ray crystallographic study helped us to understand the formation of Ni-NPs along with formation of a boron(III) compound during this reaction.
- Das, Arpan,Hota, Pradip Kumar,Mandal, Swadhin K.
-
-
- Hydrogenation of (Hetero)aryl Boronate Esters with a Cyclic (Alkyl)(amino)carbene–Rhodium Complex: Direct Access to cis-Substituted Borylated Cycloalkanes and Saturated Heterocycles
-
We herein report the hydrogenation of substituted aryl- and heteroaryl boronate esters for the selective synthesis of cis-substituted borylated cycloalkanes and saturated heterocycles. A cyclic (alkyl)(amino)carbene-ligated rhodium complex with two dimethyl groups at the ortho-alkyl scaffold of the carbene showed high reactivity in promoting the hydrogenation, thereby enabling the hydrogenation of (hetero)arenes with retention of the synthetically valuable boronate group. This process constitutes a clean, atom-economic, as well as chemo- and stereoselective route for the generation of cis-configured, diversely substituted borylated cycloalkanes and saturated heterocycles that are usually elusive and difficult to prepare.
- Ling, Liang,He, Yuan,Zhang, Xue,Luo, Meiming,Zeng, Xiaoming
-
supporting information
p. 6554 - 6558
(2019/04/17)
-
- Visible-Light-Induced Organocatalytic Borylation of Aryl Chlorides
-
The preparation of arylboronates from unactivated aryl chlorides in a transition-metal-free manner is rather challenging. There are only few examples to achieve this goal by using ultraviolet irradiation. Based on the mechanistic understanding of the diboron/methoxide/pyridine reaction system, we achieved photoactivation of the in situ generated super electron donor and developed a visible-light-induced organocatalytic method for efficient borylation of unactivated aryl chlorides.
- Zhang, Li,Jiao, Lei
-
supporting information
p. 9124 - 9128
(2019/06/17)
-
- Copper-catalysed borylation of aryl chlorides
-
We report herein the first Cu-catalysed borylation of a wide range of aryl chlorides with different electronic and steric properties using a readily prepared NHC-stabilised Cu catalyst and KOtBu as the base with B2pin2 (pin = pinacolato) as the boron reagent. The aryl chlorides are converted into their corresponding arylboronic esters in good yields. The new procedure shows broad functional group tolerance, and B2neop2 (neop = neopentyl glycolato) can also be applied as the boron reagent.
- Kuehn, Laura,Huang, Mingming,Radius, Udo,Marder, Todd B.
-
supporting information
p. 6601 - 6606
(2019/07/16)
-
- Additive- and Photocatalyst-Free Borylation of Arylazo Sulfones under Visible Light
-
We developed a photocatalyst-free and additive-free, visible light induced borylation reaction using arylazo sulfones as starting material. This protocol shows some advantages such as mild conditions, simple equipment, and wide substrate scope, which gives a complementary protocol for the preparation of arylboronates.
- Xu, Yuliang,Yang, Xinying,Fang, Hao
-
p. 12831 - 12837
(2018/10/20)
-
- Nickel-catalysed decarbonylative borylation of aroyl fluorides
-
The first Ni(cod)2/PPh3 catalyst system has been established for decarbonylative borylation of aroyl fluorides with bis(pinacolato)diboron. A wide range of functional groups in the substrates were well tolerated. The ease of access of the starting aroyl fluorides indicates that these results might become an alternative to the existing decarbonylation events.
- Wang, Zhenhua,Wang, Xiu,Nishihara, Yasushi
-
supporting information
p. 13969 - 13972
(2019/01/03)
-
- Palladium-Catalyzed Decarbonylative Borylation of Carboxylic Acids: Tuning Reaction Selectivity by Computation
-
Decarbonylative borylation of carboxylic acids is reported. Carbon electrophiles are generated directly after reagent-enabled decarbonylation of the in situ accessible sterically-hindered acyl derivative of a carboxylic acid under catalyst controlled conditions. The scope and the potential impact of this method are demonstrated in the selective borylation of a variety of aromatics (>50 examples). This strategy was used in the late-stage derivatization of pharmaceuticals and natural products. Computations reveal the mechanistic details of the unprecedented C?O bond activation of carboxylic acids. By circumventing the challenging decarboxylation, this strategy provides a general synthetic platform to access arylpalladium species for a wide array of bond formations from abundant carboxylic acids. The study shows a powerful combination of experiment and computation to predict decarbonylation selectivity.
- Liu, Chengwei,Ji, Chong-Lei,Hong, Xin,Szostak, Michal
-
p. 16721 - 16726
(2018/11/30)
-
- Cobalt-Catalyzed C-F Bond Borylation of Aryl Fluorides
-
A mild and practical cobalt-catalyzed defluoroborylation of fluoroarenes is presented for the first time. The method permits straightforward functionalization of fluoroarenes, with high selectivity for borylation of C-F over C-H bonds, and a tolerance for aerobic conditions. Furthermore, two-step 18F-fluorination was achieved for expanding the scope of 18F-positron emission tomography probes.
- Lim, Soobin,Song, Dalnim,Jeon, Seungwon,Kim, Youngsuk,Kim, Hyunseok,Lee, Sanghee,Cho, Hyungdo,Lee, Byung Chul,Kim, Sang Eun,Kim, Kimoon,Lee, Eunsung
-
supporting information
p. 7249 - 7252
(2018/11/23)
-
- Metal-Free and Redox-Neutral Conversion of Organotrifluoroborates into Radicals Enabled by Visible Light
-
Converting organoboron compounds into the corresponding radicals has broad synthetic applications in organic chemistry. To achieve these transformations, various strong oxidants such as Mn(OAc)3, AgNO3/K2S2O8, and Cu(OAc)2, in stoichiometric amounts are required, proceeding by a single-electron transfer mechanism. Established herein is a distinct strategy for generating both aryl and alkyl radicals from organotrifluoroborates through an SH2 process. This strategy is enabled by using water as the solvent, visible light as the energy input, and diacetyl as the promoter in the absence of any metal catalyst or redox reagent, thereby eliminating metal waste. To demonstrate its synthetic utility, an efficient acetylation to prepare valuable aryl (alkyl) methyl ketones is described and applications to construct C?C, C?I, C?Br, and C?S bonds are also feasible. Experimental evidence suggests that triplet diacetyl serves as the key intermediate in this process.
- Liu, Wenbo,Liu, Peng,Lv, Leiyang,Li, Chao-Jun
-
supporting information
p. 13499 - 13503
(2018/09/25)
-