- Synthesis of Decahydrocyclobuta[cd]indene Skeletons: Rhodium(III)-Catalyzed Hydroarylation and Relay Thiophene-Promoted Intramolecular [2+2] Cycloaddition
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The preparation of decahydrocyclobuta[cd]indene skeleton was accomplished through rhodium(III)-catalyzed hydroarylation and relay thiophene-promoted intramolecular [2+2] cycloaddition. This tandem reaction exhibited broad substrate scope (24 examples) and good functional group compatibility. Control experiments revealed the important role of sulfur (S) heteroatom, thus a tentative mechanism with thiophene-promoted double Michael additions was proposed to explain this formal [2+2] cycloaddition. Moreover, the resulting polycyclic products displayed potent anti-cancer activities against breast cancer cell lines MDA-MB-468. (Figure presented.).
- Gao, Dingding,Wang, Feng,Liu, Xing-Yu,Feng, Kai-Rui,Zhao, Jia-Ying,Wang, Yu-Hui,Yang, Xiao-Di,Tian, Ping,Lin, Guo-Qiang
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supporting information
p. 4384 - 4390
(2020/09/23)
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- Copper-catalyzed cross-coupling of aryl-, primary alkyl-, and secondary alkylboranes with heteroaryl bromides
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A method for the Cu-catalyzed cross-coupling of both aryl and alkylboranes with aryl bromides is described. The method employs an inexpensive Cu-catalyst and functions for a variety of heterocyclic as well as electron deficient aryl bromides. In addition, aryl iodides of varying substitution patterns and electronic properties work well.
- Bergmann, Allison M.,Oldham, Adam M.,You, Wei,Brown, M. Kevin
-
supporting information
p. 5381 - 5384
(2018/06/01)
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- The Highly Efficient Suzuki–Miyaura Cross-Coupling of (Hetero)aryl Chlorides and (Hetero)arylboronic Acids Catalyzed by “Bulky-yet-Flexible” Palladium–PEPPSI Complexes in Air
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A series of Pd–PEPPSI complexes were designed and synthesized. The relationship between catalyst structure and properties was systematically investigated. It was revealed that “bulky-yet-flexible” C3 bearing ancenaphthyl backbone was a highly efficient precatalyst and could be successfully employed in Suzuki–Miyaura reactions of (hetero)aryl chlorides with (hetero)arylboronic acids at a low palladium loading in the presence of a weak inorganic base in air.
- Ouyang, Jia-Sheng,Li, Yan-Fang,Huang, Fei-Dong,Lu, Dong-Dong,Liu, Feng-Shou
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p. 371 - 375
(2017/12/15)
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- Cobalt-Catalyzed Cross-Coupling Reactions of Arylboronic Esters and Aryl Halides
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An efficient cobalt catalyst system for the Suzuki-Miyaura cross-coupling reaction of arylboronic esters and aryl halides has been identified. In the presence of cobalt(II)/terpyridine catalyst and potassium methoxide, a diverse array of (hetero)biaryls have been prepared in moderate to excellent yields.
- Duong, Hung A.,Wu, Wenqin,Teo, Yu-Yuan
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supporting information
p. 4363 - 4366
(2017/12/05)
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- Piperidine-appended imidazolium ionic liquid as task-specific basic-IL for Suzuki and Heck reactions and for tandem Wittig-Suzuki, Wittig-Heck, Horner-Emmons-Suzuki, and Horner-Emmons-Heck protocols
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Facile, high yielding, one-pot methods for the synthesis of a library of diversely substituted bi-aryls, diarylethenes, and aryl-enoates, via Suzuki and Heck reactions, and by sequential Wittig-Suzuki, Wittig-Heck, Horner-Emmons-Suzuki, and Horner-Emmons-Heck reactions are reported. The reactions employ piperidine-appended imidazolium ionic liquid [PAIM][NTf2] as a task-specific basic-IL, butyl-methyl-imidazolium ionic liquid [BMIM][X] (X?=?PF6, BF4) as solvent, and catalytic amounts of Pd(OAc)2 with no other additives. Wittig and Horner-Emmons reactions are effected by reacting substituted benzaldehydes with 4-bromobenzyl-PPh3 (or bromomethyl-PPh3) phosphonium salts, or diethylphosphonate with bromobenzaldehydes respectively, to form the corresponding ethenes. Subsequent cross-coupling reactions are accomplished by addition of aryl-boronic acid or phenyl-ethenes along with Pd(OAc)2 to bring about the aforementioned hyphenated transformations. The feasibility to perform double-olefination via Wittig and Horner-Emmons reactions with dialdehydes to form highly conjugated bis-styryl and bis-enoate compounds is also shown. The [BMIM][X] solvent is recycled and reused.
- Savanur, Hemantkumar M.,Kalkhambkar, Rajesh G.,Laali, Kenneth K.
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p. 150 - 161
(2017/06/30)
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- Sodium Chloride Catalyzed Regioselective Trifluoromethylthiolation of Furans
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Here, we report the catalytic trifluoromethylthiolation of furans employing sodium chloride as an inexpensive, abundant and ecologically friendly catalyst. The developed method exhibits perfect regioselectivity and a high functional group tolerance. Furth
- Ernst, Johannes B.,Rakers, Lena,Glorius, Frank
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supporting information
p. 260 - 268
(2016/12/24)
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- Ru-Catalyzed Regioselective Direct Hydroxymethylation of (Hetero)Arenes via C-H Activation
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An efficient and direct ruthenium-catalyzed regioselective hydroxymethylation of (hetero)arenes via C-H activation with paraformaldehyde as a hydroxymethylating reagent is described. The corresponding products can be obtained in good to excellent yield. A number of aryl aldehydes can also be used in place of paraformaldehyde giving the desired alcohol products with similarly good results.
- Zhang, Guo-Fu,Li, Yue,Xie, Xiao-Qiang,Ding, Cheng-Rong
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supporting information
p. 1216 - 1219
(2017/03/14)
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- Cobalt-catalyzed C-H cyanation of (Hetero)arenes and 6-Arylpurines with N -cyanosuccinimide as a new cyanating agent
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A cobalt-catalyzed C-H cyanation reaction of arenes has been developed using N-cyanosuccinimide as a new electrophilic cyanating agent. The reaction proceeds with high selectivity to afford monocyanated products with excellent functional group tolerance. Substrate scope was found to be broad enough to include a wide range of heterocycles including 6-arylpurines.
- Pawar, Amit B.,Chang, Sukbok
-
supporting information
p. 660 - 663
(2015/03/04)
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- Palladacycle-catalyzed Suzuki-Miyaura reaction of aryl/heteroaryl halides with MIDA boronates in EtOH/H2O or H2O
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With good to excellent yields, a series of mono- or diheteroaryl compounds were synthesized via the palladacycle-catalyzed Suzuki-Miyaura reaction of various N-methyliminodiacetic acid (MIDA) boronates with aryl/heteroaryl halides in EtOH/H2O or H2O. This journal is the Partner Organisations 2014.
- Li, Yabo,Wang, Jingran,Wang, Zhiwei,Huang, Mengmeng,Yan, Beiqi,Cui, Xiuling,Wu, Yusheng,Wu, Yangjie
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p. 36262 - 36266
(2014/11/08)
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- Nickel-catalyzed cross-coupling of aryl fluorides and organozinc reagents
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Ni(PCy3)2Cl2 was demonstrated to effectively catalyze cross-coupling of aryl fluorides and organozinc reagents. Both electron-poor and -rich aryl fluorides can react effectively with nucleophiles including aryl-, methyl-, and benzylzinc chlorides. A wide range of substituents and functional groups are tolerated. In the presence of a directing group, PhC(O), the reaction is selective for cleavage of the C-F bond ortho to the carbonyl substituent in a difluoroarene.
- Zhu, Feng,Wang, Zhong-Xia
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p. 4285 - 4292
(2014/06/09)
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- Regioselective ruthenium-catalyzed carbonylative direct arylation of five-membered and condensed heterocycles
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A ruthenium-catalyzed carbonylative Ci£H bond arylation process for the three-component synthesis of complex aryl-(hetero)aryl ketones in an aqueous solution has been developed. By exploiting the ortho-activating effect of nitrogen-containing directing groups, a regioselective, successive twofold C(sp2)i£C(sp2) bond formation has been achieved. This straightforward catalytic process provides access to versatile products prevalent in multiple bioactive compounds and supplies a valuable functional group for subsequent transformations. Ci£ H bond functionalization: A ruthenium-catalyzed carbonylative Ci£H bond arylation process for the three-component synthesis of complex aryl-(hetero)aryl ketones in an aqueous solution has been developed (see scheme). By exploiting the ortho-activating effect of nitrogen-containing directing groups, a regioselective, successive twofold C(sp2) i£C(sp2) bond formation has been achieved.
- Pospech, Jola,Tlili, Anis,Spannenberg, Anke,Neumann, Helfried,Beller, Matthias
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supporting information
p. 3135 - 3141
(2014/03/21)
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- General suzuki coupling of heteroaryl bromides by using tri-tert-butylphosphine as a supporting ligand
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A general procedure for the fast Suzuki coupling of major families of heteroaryl bromides was realized by using Pd(OAc)2/PtBu3 as the catalyst. Many couplings were finished within minutes at room temperature in n-butanol. Different from previous studies, three typical heteroaryl bromides were systematically examined in couplings of various heteroaryl and aryl boronic acids. A fast, general coupling of heteroaryl bromides is realized by using a single palladium catalyst supported by tri-tert-butylphosphine.
- Zou, Yinjun,Yue, Guizhou,Xu, Jianwei,Zhou, Jianrong
-
supporting information
p. 5901 - 5905
(2015/03/30)
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- Highly reactive, single-component nickel catalyst precursor for Suzuki-Miyuara cross-coupling of heteroaryl boronic acids with heteroaryl halides
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One for all: The coupling of a range of nitrogen- and sulfur-containing heteroaryl halides with five-membered nitrogen-, oxygen-, and sulfur-containing heteroaryl boronic acids were achieved in high yields with only 0.5 mol % of the single-component nickel precatalyst [(dppf)NiCl(cinnamyl)] (dppf=1,1′- bis(diphenylphosphanyl)ferrocene). The reaction demonstrates good functional group compatibility, and is easily conducted on a large scale without a dry box. Copyright
- Ge, Shaozhong,Hartwig, John F.
-
supporting information
p. 12837 - 12841
(2013/02/22)
-
- Nickel complexes supported by quinoline-based ligands: Synthesis, characterization and catalysis in the cross-coupling of arylzinc reagents and aryl chlorides or aryltrimethylammonium salts
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Lithium and nickel complexes bearing quinoline-based ligands have been synthesized and characterized. Reaction of 8-azidoquinoline with Ph 2PNHR (R = p-MeC6H4, But) affords N-(8-quinolyl)iminophosphoranes RNHP(Ph2)N(8-C9H 6N) (1a, R = p-MeC6H4; 1b, R = But. C9H6N = quinolyl)). Reaction of 1a with (DME)NiCl 2 generates a nickel complex [NiCl2{N(8-C 9H6N)P(Ph2)NH(p-MeC6H4)}] (2a). Treatment of 1b with (DME)NiCl2 and following with NaH produces [NiCl{(1,2-C6H4)P(Ph)(NHBut)N(8-C 9H6N)}] (4). Complex 4 was also obtained by reaction of (DME)NiCl2 with [Li{(1,2-C6H4)P(Ph)(NHBu t)N(8-C9H6N)}] (5) prepared through lithiation of 1b. Reaction of 2-PyCH2P(Ph2)N(8-C9H 6N) (6, Py = pyridyl) and PhNC(Ph)CH2P(Ph 2)N(8-C9H6N) (8), respectively, with (DME)NiCl2 yields two five-coordinate N,N,N-chelate nickel complexes, [NiCl2{2-PyCH2P(Ph2)N(8-C9H 6N)}] (7) and [NiCl2{PhNC(Ph)CH2P(Ph 2)N(8-C9H6N)}] (9). Similar reaction between Ph2PCH2P(Ph2)N(8-C9H6N) (10) and (DME)NiCl2 results in five-coordinate N,N,P-chelate nickel complex [NiCl2{Ph2PCH2P(Ph2)N(8- C9H6N)}] (11). Treatment of [(8-C9H 6N)NP(Ph2)]2CH2 (12) [prepared from (Ph2P)2CH2 and 2 equiv. of 8-azidoquinoline] with LiBun and (DME)NiCl2 successively affords [NiCl{(8-C9H6N)NP(Ph2)}2CH] (13). The new compounds were characterized by 1H, 13C and 31P NMR spectroscopy (for the diamagnetic compounds), IR spectroscopy (for the nickel complexes) and elemental analysis. Complexes 2a, 4, 7, 9, 11 and 13 were also characterized by single-crystal X-ray diffraction techniques. The nickel complexes were evaluated for the catalysis in the cross-coupling reactions of arylzinc reagents with aryl chlorides and aryltrimethylammonium salts. Complex 7 exhibits the highest activity among the complexes in catalyzing the reactions of arylzinc reagents with either aryl chlorides or aryltrimethylammonium bromides.
- Zhang, Qiang,Zhang, Xue-Qi,Wang, Zhong-Xia
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p. 10453 - 10464,12
(2020/08/31)
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- Cross-coupling of aryltrimethylammonium iodides with arylzinc reagents catalyzed by amido pincer nickel complexes
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The cross-coupling reaction of aryltrimethylammonium iodides with aryl- or heteroarylzinc chlorides catalyzed by amido pincer nickel complexes was performed. The reaction requires low catalyst loading and displays broad substrate scope.
- Zhang, Xue-Qi,Wang, Zhong-Xia
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experimental part
p. 3658 - 3663
(2012/05/20)
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- PdCl2(dppf)-catalyzed in situ coupling of 2-hydroxypyridines with aryl boronic acids mediated by PyBroP and the one-pot chemo- and regioselective construction of two distinct aryl-aryl bonds
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We present a PdCl2(dppf)-catalyzed synthesis of 2-arylated pyridine derivatives via the in situ coupling of 2-OH pyridines and boronic acids mediated by PyBroP. In addition, the highly chemo- and regioselective construction of two different aryl-aryl bonds via a one-pot operation has also been demonstrated by the orthogonal use of this method with the Ni-catalyzed Suzuki-Miyaura coupling of phenols.
- Li, Shui-Ming,Huang, Jie,Chen, Guo-Jun,Han, Fu-She
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supporting information; experimental part
p. 12840 - 12842
(2012/01/05)
-
- Rhodium(I)-catalyzed direct carboxylation of arenes with CO2 via chelation-assisted C-H bond activation
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Rh-catalyzed direct carboxylation of unactivated aryl C-H bond under atmospheric pressure of carbon dioxide was realized via chelation-assisted C-H activation for the first time. Variously substituted and functionalized 2-arylpyridines and 1-arylpyrazoles underwent the carboxylation in the presence of the rhodium catalyst and a stoichiometric methylating reagent, AlMe 2(OMe), to give carboxylated products in good yields. The catalysis is proposed to consist of methylrhodium(I) species as the key intermediate, which undergoes C-H activation to afford rhodium(III), followed by reductive elimination of methane to give nucleophilic arylrhodium(I). This approach demonstrates promising application of C-H bond activation strategy in the field of carbon dioxide fixation.
- Mizuno, Hajime,Takaya, Jun,Iwasawa, Nobuharu
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supporting information; experimental part
p. 1251 - 1253
(2011/04/16)
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- Palladium-catalyzed indole, pyrrole, and furan arylation by aryl chlorides
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The palladium-catalyzed direct arylation of indoles, pyrroles, and furans by aryl chlorides has been demonstrated. The method employs a palladium acetate catalyst, 2-(dicyclohexylphosphino)-biphenyl ligand, and an inorganic base. Electron-rich and electron-poor aryl chlorides as well as chloropyridine coupling partners can be used, and arylated heterocycles are obtained in moderate to good yields. Optimization of base, ligand, and solvent is required for achieving best results.
- Nadres, Enrico T.,Lazareva, Anna,Daugulis, Olafs
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experimental part
p. 471 - 483
(2011/04/15)
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- Dual effect of halides in the stille reaction: In situ halide metathesis and catalyst stabilization
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Halide anions can increase or decrease the transmetallation rate of the Stille reaction through in situ halide metathesis. Although the influence of the halogen present in oxidative addition complexes on the transmetallation rate with organostannanes was already known, the application of in situ halide metathesis to accelerate cross-coupling reactions with organometallic reagents is not described in the literature yet. In addition a second unprecedented role of halides was discovered. Halide anions stabilize the [Pd0(L) 2] catalyst in Stille reactions, by means of [Pd0X(L) 2]? formation (X=Cl, I), hereby preventing its leaching from the catalytic cycle. Both arene (iodobenzene) and azaheteroarene (2-halopyridine, halopyrazine, 2-halopyrimidine) substrates were used.
- Verbeeck, Stefan,Meyers, Caroline,Franck, Philippe,Jutand, Anny,Maes, Bert U. W.
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experimental part
p. 12831 - 12837
(2011/02/25)
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- Palladium on charcoal-catalyzed ligand-free Stille coupling
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An efficient ligand-free Stille coupling reaction catalyzed by palladium on charcoal was developed. Tetraphenyltin was reacted with a variety of aryl halides including aryl chlorides using LiCl as an additive. The reactions of tributyl organotin compounds with aryl iodides were effectively expedited by the addition of LiF. These reactions efficiently proceeded without a phosphine or arsenic ligand and no leached palladium was detected in the reaction mixture.
- Yabe, Yuki,Maegawa, Tomohiro,Monguchi, Yasunari,Sajiki, Hironao
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experimental part
p. 8654 - 8660
(2010/11/19)
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- Synthesis of amido-N-imidazolium salts and their applications as ligands in suzuki-miyaura reactions: Coupling of hetero- aromatic halides and the synthesis of milrinone and irbesartan
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A new catalytic system based on palladium-amido-N-heterocyclic carbenes for Suzuki-Miyaura coupling reactions of heteroaryl bromides is described. A variety of sterically bulky, amido-N-imidazolium salts were synthesized in high yields from the corresponding anilines. This catalytic system effectively promoted Suzuki-Miyaura couplings of heteroaryl bromides and chlorides with a range of boronic acids to give the corresponding aryl compounds in high yield. The yield was increased with increasing steric bulkiness of the substituted group. Especially, 1-(2,6-diisopropylphenyl)-3-N-(2,4,6-tri-tert- butylphenylacetamido)imidazolium bromide (4bc) exhibited 850,000 TON in the coupling reaction of 2-bromopyridine and phenylboronic acid. In addition, pharmaceutical compounds such as milrinone and irbesartan were synthesized via Suzuki-Miyaura coupling using sterically bulky, amido-N-imidazolium salt (4bc) as a ligand. Copyright
- Kumar, Manian Rajesh,Park, Kyungho,Lee, Sunwoo
-
supporting information; experimental part
p. 3255 - 3266
(2011/02/23)
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- Deprotonative metalation of substituted benzenes and heteroaromatics using amino/alkyl mixed lithium-zinc combinations
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Different homoleptic and heteroleptic lithium-zinc combinations were prepared, and structural elements obtained on the basis of NMR spectroscopic experiments and DFT calculations. In light of their ability to metalate anisole, pathways were proposed to justify the synergy observed for some mixtures. The best basic mixtures were obtained either by combining ZnCl 2·TMEDA (TMEDA = N,N,N',N'tetramethylethylenediamine) with [Li(tmp)] (tmp = 2,2,6,6-tetramethylpiperidino; 3 equiv) or by replacing one of the tmp in the precedent mixture with an alkyl group. The reactivity of the aromatic lithium zincates supposedly formed was next studied, and proved to be substrate-, base-, and electrophile-dependent. The aromatic lithium zincates were finally involved in palladium-catalyzed cross-coupling reactions with aromatic chlorides and bromides.
- Snegaroff, Katia,Komagawa, Shinsuke,Chevallier, Floris,Gros, Philippe C.,Golhen, Stephane,Roisnel, Thierry,Uchiyama, Masanobu,Mongin, Florence
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experimental part
p. 8191 - 8201
(2010/09/11)
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- Scope of the suzuki-Miyaura cross-coupling reactions of potassium heteroaryltrifluoroborates
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A wide variety of bench-stable potassium heteroaryltrifluoroborates were prepared, and general reaction conditions were developed for their cross-coupling to aryl and heteroaryl halides. The cross-coupled products were obtained in good to excellent yields. This method represents an efficient and facile installation of heterocyclic building blocks onto preexisting organic substructures.
- Molander, Gary A.,Canturk, Belgin,Kennedy, Lauren E.
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supporting information; experimental part
p. 973 - 980
(2009/07/11)
-
- Efficient cross-coupling of aryl chlorides with arylzinc reagents catalyzed by amido pincer complexes of nickel
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The nickel-catalyzed Negishi cross-coupling reaction of aryl chlorides with arylzinc compounds was investigated. The nickel complexes with the amido pincer type of ligands exhibited high catalytic activity and good functional group tolerance.
- Wang, Li,Wang, Zhong-Xia
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p. 4335 - 4338
(2008/03/11)
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- Deprotonation of furans using lithium magnesates
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Furan was deprotonated on treatment with 1/3 equiv of Bu3MgLi in THF at rt. The lithium arylmagnesate formed was either trapped with electrophiles or involved in a palladium-catalyzed cross-coupling reaction with 2-bromopyridine. The highly coordinated magnesate Bu4MgLi2 (1/3 equiv) proved to be a better deprotonating agent than Bu3MgLi; the monitoring of the reaction using NMR spectroscopy showed that the deprotonation of furan at rt required 2 h whereas the subsequent electrophilic trapping was instantaneous. The method was extended to benzofuran, allowing its functionalization at C2 in high yields. The deprotonation of 2-methylfuran and lithium furfurylalkoxide at C5 turned out to be difficult, requiring either long reaction times or higher temperatures.
- Mongin, Florence,Bucher, Aurélien,Bazureau, Jean Pierre,Bayh, Omar,Awad, Ha?an,Trécourt, Fran?ois
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p. 7989 - 7992
(2007/10/03)
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- PROCESS FOR PRODUCING 2-SUBSTITUTED PYRIDINE DERIVATIVE
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The present invention provides a method of producing a pyridine derivative having a substituent at the 2-position of a heterocyclic structure conveniently and with fine selectivity. The present invention relates to a production method of a pyridine derivative having a substituent at the 2-position of a heterocyclic structure, which is represented by the formula (III), which includes reacting a 2-sulfonylpyridine derivative of the formula (I) with an organometallic compound of the formula (II) and the like, and the like: wherein each symbol is as defined in the Description.
- -
-
Page/Page column 12-13
(2008/06/13)
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- Pyridine ring formation through the photoreaction of arenecarbothioamides with diene-conjugated carbonyl compounds
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Irradiation of arenecarbothioamides with hexa-2,4-dienal in benzene solution gives 2-arylpyridines in moderate yields.
- Oda, Kazuaki,Nakagami, Rikiji,Nishizono, Naozumi,Machida, Minoru
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p. 2371 - 2372
(2007/10/03)
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- Novel base-initiated reactions of N-substituted pyridinium salts
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Reaction of N-fluoropyridinium triflate with a base in dichloromethane gave 2-chloropyridine as the major product along with 2-pyridyl triflate and 2-fluoropyridine, regardless of the nature of the base. This base-initiated reaction was also shown to take place similarly in other halogenated alkanes, ethers, a nitrile, aromatics, a ketone, vinyl ethers, alcohols and trimethylsilyl acetate as solvents to give pyridine derivatives substituted with a solvent molecule (s) at the 2-position. N-(Trifluoromethanesulfonyloxy)-and (benzenesulfonyloxy) pyridinium salts were found to undergo the same base-initiated reaction. These reactions may be explained by a postulated singlet carbene (canonical formula 11b) produced through proton abstraction of N-substituted pyridinium salts. A similar carbene reaction may thus likely occur in the thermal decomposition of thiatriazole 10. Ab initio MO calculations revealed the structure and properties of the labile deprotonated N-fluoropyridinium cation and supported the carbene intermediate reaction mechanism rather than a pyridynium or pyridyl cation mechanism. Quarroz's reports on the reactions of picolinic acid N-oxide and the reported reactions of pyridines with F2, CH3COOF or CsSO4F in solvents may be explained by this carbene mechanism.
- Umemoto, Teruo,Tomizawa, Ginjiro,Hachisuka, Hitoharu,Kitano, Masakatsu
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p. 161 - 168
(2007/10/03)
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- BASE-INITIATED REACTIONS OF N-FLUOROPYRIDINIUM SALTS; A NOVEL CYCLIC CARBENE PROPOSED AS A REACTIVE SPECIES
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A new type of base-initiated reactions of pyridinium salts was found and a novel cyclic carbene was proposed as the reactive species.
- Unemoto, Teruo,Tomizawa, Ginjiro
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p. 2705 - 2708
(2007/10/02)
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- PHOTO-ARYLATION III : SYNTHESIS OF 2-HETEROARYLPYRIDINES
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The title compounds were prepared in satisfactory yields by photo-reaction of 2-halopyridine (halogen; I,Br) with five membered heteroaromatics.
- Seki, Koh-ichi,Ohkura, Kazue,Terashima, Masanao,Kanaoka, Yuichi
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p. 2347 - 2350
(2007/10/02)
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- Preparation of α- and γ-(α-furyl)pyridines
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Mixtures of isomeric alkyl-substituted (in the pyridine ring) α- and γ-(α-furyl)-pyridines were obtained in up to ~40% yields by condensation of furfural and ammonia with several aliphatic ketones and aldehydes (at 370-380 °C with a cadmium calcium phosphate catalyst). The dependence of the yields and structures of the corresponding isomers on the structure of the starting carbonyl compound was examined. Data from the PMR and mass spectra were used to prove the structures of the pyridine bases obtained.
- Prostakov,Radzhan,Soldatenkov,Mikaya
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p. 284 - 289
(2007/10/02)
-