cas 195062-62-5, ETHYL 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOATE

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Synthesis of arylboronates via the Pd-catalyzed desulfitative coupling reaction of sodium arylsulfinates with bis(pinacolato)diboron
The desulfitative borylation reaction of sodium arylsulfinates with bis(pinacolato)diboron or bis(neopentylglycolato)diboron under palladium catalysis has been developed, allowing selective C-B bond formation to give arylboronates with a range of functional groups in moderate to good yields under mild reaction conditions. A gram-scale preparation as well as the cascade Suzuki-Miyaura cross-coupling of arylboronates demonstrated the potential practical utility in organic synthesis.
Qiu, Di,Li, Songyi,Yue, Guanglu,Mao, Jinshan,Xu, Bei,Yuan, Xinyu,Ye, Fei
supporting information

(2021/11/04)

Light- and Manganese-Initiated Borylation of Aryl Diazonium Salts: Mechanistic Insight on the Ultrafast Time-Scale Revealed by Time-Resolved Spectroscopic Analysis
Manganese-mediated borylation of aryl/heteroaryl diazonium salts emerges as a general and versatile synthetic methodology for the synthesis of the corresponding boronate esters. The reaction proved an ideal testing ground for delineating the Mn species responsible for the photochemical reaction processes, that is, involving either Mn radical or Mn cationic species, which is dependent on the presence of a suitably strong oxidant. Our findings are important for a plethora of processes employing Mn-containing carbonyl species as initiators and/or catalysts, which have considerable potential in synthetic applications.
Firth, James D.,Hammarback, L. Anders,Burden, Thomas J.,Eastwood, Jonathan B.,Donald, James R.,Horbaczewskyj, Chris S.,McRobie, Matthew T.,Tramaseur, Adam,Clark, Ian P.,Towrie, Michael,Robinson, Alan,Krieger, Jean-Philippe,Lynam, Jason M.,Fairlamb, Ian J. S.
supporting information
p. 3979 - 3985
(2021/02/03)

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)

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)

Luminescent iridium(iii)-boronic acid complexes for carbohydrate sensing
A family of four Ir(iii) complexes of the form [Ir(ppy)2(L)]Cl (where ppy = 2-phenyl-pyridine and L = a pyridyl-1,2,4-triazole or pyridyl-1,3,4-oxadiazole ligand bearing a boronic acid group) have been prepared as potential luminescent sensors for carbohy
Agugiaro, Johnny,Barnard, Peter J.,Haghighatbin, Mohammad A.,Hashemzadeh, Tahmineh,Hogan, Conor F.,Wilson, David J. D.
supporting information
p. 11361 - 11374
(2020/09/02)

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)

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)

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-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)

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)

Photoinduced Miyaura Borylation by a Rare-Earth-Metal Photoreductant: The Hexachlorocerate(III) Anion
The first photoinduced carbon(sp2)–heteroatom bond forming reaction by a rare-earth-metal photoreductant, a Miyaura borylation, has been achieved. This simple, scalable, and novel borylation method that makes use of the hexachlorocerate(III) anion ([CeIIICl6]3?, derived from CeCl3) has a broad substrate scope and functional-group tolerance and can be conducted at room temperature. Combined with Suzuki–Miyaura cross-coupling, the method is applicable to the synthesis of various biaryl products, including through the use of aryl chloride substrates.
Qiao, Yusen,Yang, Qiaomu,Schelter, Eric J.
supporting information
p. 10999 - 11003
(2018/07/31)

Alcohol-initiated dediazoniation of aryldiazonium ions to aryl radicals: A simple and efficient route to arylboronates
A simple and efficient access to arylboronates was achieved with methanol-initiated borylation of aryldiazonium salts. Reduction of aryldiazonium ions by single electron transfer from methanol affords aryl radical species, which undergo a subsequent C?B bond formation with bis(pinacolato)diboron. This highly practical borylation process, which can be carried out on the gram-scale, enjoys operational simplicity as well as mild and catalyst-free conditions.
Zhang, Xiulian,Zhang, Zhicheng,Xie, Yongbin,Jiang, Yujie,Xu, Ruibo,Luo, Yuhui,Tao, Chuanzhou
p. 481 - 485
(2018/10/15)

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)

An organic boron compound
PROBLEM TO BE SOLVED: To provide a production method of an arylboronic acid ester with a wide range of application substrate, using no heavy metal.SOLUTION: An organic halogen compound represented by the general formula R-X (where, X is Br or I; R is a C1 to 20 alkyl group, a C6 to 14 aryl group, a heterocyclic group comprising 1 to 3 hetero atoms selected from N, O and S, or the like) and a compound represented by the general formula (VI) are reacted in the presence of sodium alkoxide or potassium alkoxide for substitution of a substituted Si moiety and the R moiety to obtain arylboronic acid ester. (In the formula, three Rare each independently a C1 to 6 alkyl group or a C6 to 10 aryl group; and four Reach independently a C1 to 3 alkyl group.)
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Paragraph 0072-0074; 0096-0097

(2019/02/20)

Noncovalent Interactions in Ir-Catalyzed C-H Activation: L-Shaped Ligand for Para-Selective Borylation of Aromatic Esters
An efficient strategy for the para-selective borylation of aromatic esters is described. For achieving high para-selectivity, a new catalytic system has been developed modifying the core structure of the bipyridine. It has been proposed that the L-shaped ligand is essential to recognize the functionality of the oxygen atom of the ester carbonyl group via noncovalent interaction, which provides an unprecedented controlling factor for para-selective C-H activation/borylation.
Hoque, Md Emdadul,Bisht, Ranjana,Haldar, Chabush,Chattopadhyay, Buddhadeb
supporting information
p. 7745 - 7748
(2017/06/21)

N-HYDROXYFORMAMIDE COMPOUNDS AND COMPOSITIONS COMPRISING THEM FOR USE AS BMP1, TLL1 AND/OR TLL2 INHIBITORS
Compounds of Formulas (I) and (II) and salts thereof; methods of making and using the same, including use for inhibiting BMP1, TLL1 and/or TLL2 and in treatment of diseases associated with BMP1, TLL1 and/or TLL2 activity.
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(2017/01/26)

Convenient and General Zinc-Catalyzed Borylation of Aryl Diazonium Salts and Aryltriazenes under Mild Conditions
A convenient and general zinc-catalyzed borylation of aryl diazonium salts and aryltriazenes has been developed. With bis- (pinacolato)diboron as the borylation reagent, aryldiazonium tetrafluoroborate salts and aryltriazenes were transformed into the corresponding arylboronates in moderate to excellent yields under mild conditions. As a convenient and practical methodology, no additional ligands, base, or any other additives are required here.
Qi, Xinxin,Jiang, Li-Bing,Zhou, Chao,Peng, Jin-Bao,Wu, Xiao-Feng
p. 345 - 349
(2017/06/23)

Borylation of aryldiazonium salts at room temperature in an aqueous solution under catalyst-free conditions
A general and convenient borylation reaction of aryldiazonium tetrafluoroborate salts with B2pin2 has been developed. In this catalytic system, no catalyst, additional ligands or additives were required. The reaction proceeded smoothly in an aqueous solution, and a variety of arylboronates were isolated in moderate to excellent yields under mild reaction conditions.
Qi, Xinxin,Li, Hao-Peng,Peng, Jin-Bao,Wu, Xiao-Feng
supporting information
p. 3851 - 3853
(2017/09/15)

Pyridine-catalyzed radical borylation of aryl halides
A pyridine-catalyzed transition-metal-free borylation reaction of haloarenes has been developed based on the selective cross-coupling of an aryl radical and a pyridine-stabilized boryl radical. Arylboronates were produced from haloarenes under mild conditions. This borylation reaction features a broad substrate scope, operational simplicity, and gram-scale synthetic ability.
Zhang, Li,Jiao, Lei
supporting information
p. 607 - 610
(2017/05/15)

METHOD FOR COUPLING AN AROMATIC OR VINYLIC COMPOUND TO A BORON-CONTAINING COMPOUND
In one aspect, there is provided a method of coupling an aromatic or vinylic compound having a fluorosulfonate substituent to a boron-containing compound. In another aspect, there is provided a method of coupling an aromatic or vinylic compound having a h
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Paragraph 0044-0046

(2017/03/14)

Simple and Efficient Generation of Aryl Radicals from Aryl Triflates: Synthesis of Aryl Boronates and Aryl Iodides at Room Temperature
Despite the wide use of aryl radicals in organic synthesis, current methods to prepare them from aryl halides, carboxylic acids, boronic acids, and diazonium salts suffer from limitations. Aryl triflates, easily obtained from phenols, are promising aryl radical progenitors but remain elusive in this regard. Inspired by the single electron transfer process for aryl halides to access aryl radicals, we developed a simple and efficient protocol to convert aryl triflates to aryl radicals. Our success lies in exploiting sodium iodide as the soft electron donor assisted by light. This strategy enables the scalable synthesis of two types of important organic molecules, i.e., aryl boronates and aryl iodides, in good to high yields, with broad functional group compatibility in a transition-metal-free manner at room temperature. This protocol is anticipated to find potential applications in other aryl-radical-involved reactions by using aryl triflates as aryl radical precursors.
Liu, Wenbo,Yang, Xiaobo,Gao, Yang,Li, Chao-Jun
supporting information
p. 8621 - 8627
(2017/07/06)

Radical Metal-Free Borylation of Aryl Iodides
A simple metal-free borylation of aryl iodides mediated by a fluoride sp 2 -sp 3 diboron adduct is described. The reaction conditions are compatible with various functional groups. Electronic effects of substituents do not affect the borylation while steric hindrance does. The reaction proceeds via a radical mechanism in which pyridine serves to stabilize the boryl radicals, generated in situ.
Pinet, Sandra,Liautard, Virginie,Debiais, Mégane,Pucheault, Mathieu
p. 4759 - 4768
(2017/10/03)

Preparation method of aryl borate ester and allyl borate ester
The invention discloses a preparation method of aryl borate ester and allyl borate ester. The method comprises the following step: under the catalytic action of pyridine or a derivative thereof, carrying out 1) or 2) to obtain substituted boric acid ester shown as a formula I-1 or a formula I-2: 1) a reaction of a halide, bi-boric acid ester and alkoxide; 2) a reaction of a halide and a bi-boric acid ester-alkoxide complex. The method is an efficient preparation method of the aryl borate ester and the allyl borate ester. In the preparation method provided by the invention, the inexpensive pyridine or the derivative thereof is taken as a catalyst instead of a transition metal catalyst, the reaction conditions are mild, the reaction yield is high, residues of trace transition metal in a boronation product are avoided, and the cost of an aryl and allyl borate ester synthesis reaction is lowered.
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Paragraph 0073-0074; 0077

(2017/07/12)

Efficient metal-free photochemical borylation of aryl halides under batch and continuous-flow conditions
A rapid, chemoselective and metal-free C-B bond-forming reaction of aryl iodides and bromides in aqueous solution at low temperatures was discovered. This reaction is amenable to batch and continuous-flow conditions and shows exceptional functional group tolerance and broad substrate scope regarding both the aryl halide and the borylating reagent. Initial mechanistic experiments indicated a photolytically generated aryl radical as the key intermediate.
Chen, Kai,Zhang, Shuai,He, Pei,Li, Pengfei
p. 3676 - 3680
(2016/06/09)

Structural Diversity of Cadmium(II) Coordination Polymers Induced by Tuning the Coordination Sites of Isomeric Ligands
When the coordination sites of ligands were shifted, the solvothermal reactions of four positional isomeric asymmetrical pyridyldicarboxylatic acids with Cd(NO3)2 generated four new coordination polymers, [Cd(L1)(DMF)3]·DMF·H2O (1), [H2N(CH3)2]2[Cd(L2)2]·3DMF·H2O (2), [Cd(L3)(H2O)2] (3), and [Cd(L4)]·1.5DMF (4), where DMF = N,N-dimethylformamide, H2L1 = 2-(3′-carboxylphenyl)isonicotinic acid, H2L2 = 2-(4′-carboxylphenyl)isonicotinic acid, H2L3 = 5-(3′-carboxylphenyl)nicotic acid, and H2L4 = 2-(3′-pyridyl)terephthalic acid. 1 shows a rare 2D fabric structure. 2 discloses a grid-layer structure with heterochiral helical chains and in which three sets of layers stack in different directions, affording an unprecedented 2D + 2D + 2D → 3D polycatenating framework with 3D intersecting porous systems. 3 also displays a 2D layer possessing strong intralayer π···π interactions and interlayer hydrogen bonds. 4 contains a rare Cd2(COO)4 paddle-wheel unit and forms a 3D framework with 1D open channels. The carboxyl and pyridyl groups of the positional isomeric H2L1-H2L4 ligands show distinct bridging fashions, which leads to the production of versatile architectures of 1-4, and their effects on the crystal structures are discussed. 1-4 reveal solid-state photoluminescence stemming from intraligand charge transfer. 2 and 4 show high selectivity for CO2 over CH4 but with different CO2 adsorption enthalpies. Grand canonical Monte Carlo simulations identified the multiple adsorption sites in 2 for CO2.
Liu, Bo,Zhou, Hui-Fang,Hou, Lei,Wang, Jian-Ping,Wang, Yao-Yu,Zhu, Zhonghua
supporting information
p. 8871 - 8880
(2016/10/26)

Base-Free Palladium-Catalyzed Borylation of Aryl Chlorides with Diborons
The base-free palladium-catalyzed borylation of aryl chlorides with diborons was achieved. The base-free conditions offered acceptable functional group compatibility. Based on experimental and computational studies, it was shown that smooth boryl transfer from the diborons to the arylpalladium chloride was promoted by strong interaction between the Lewis acidic boron and the chlorine atom on palladium.
Yamamoto, Yutaro,Matsubara, Hiroshi,Yorimitsu, Hideki,Osuka, Atsuhiro
p. 2317 - 2320
(2016/07/28)

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
p. 61 - 65
(2016/08/04)

Cobalt-catalyzed borylation of aryl halides and pseudohalides
We report the first Co-catalyzed borylation of aryl halides and pseudohalides with bis(pinacolato)diboron (B2pin2). The synthesis of two new Co(II) complexes of oxazolinylferrocenylphosphine ligands is described. Upon activation with LiMe, the Co complex catalyzes the borylation reactions of aryl bromides, iodides, sulfonates, arenediazonium salts, and even aryl chlorides under mild conditions, providing the borylated products in excellent to moderate yields and with high functional group tolerance.
Yao, Wubing,Fang, Huaquan,Peng, Sihan,Wen, Huanan,Zhang, Lei,Hu, Aiguo,Huang, Zheng
supporting information
p. 1559 - 1564
(2016/06/09)

Rhodium-catalyzed borylation of aryl 2-pyridyl ethers through cleavage of the carbon-oxygen bond: Borylative removal of the directing group
The rhodium-catalyzed reaction of aryl 2-pyridyl ethers with a diboron reagent results in the formation of arylboronic acid derivatives via activation of the C(aryl)-O bonds. The straightforward synthesis of 1,2-disubstituted arenes was enabled through catalytic ortho C-H bond functionalization directed by the 2-pyridyloxy group followed by substitution of this group with a boryl group. Several control experiments revealed that the presence of a sp2 nitrogen atom at the 2-position of the substrate and the use of a boron-based reagent were crucial for the activation of the relatively inert C(aryl)-O bond of aryl 2-pyridyl ethers.
Kinuta, Hirotaka,Tobisu, Mamoru,Chatani, Naoto
supporting information
p. 1593 - 1600
(2015/03/05)

Making Dimethylamino a Transformable Directing Group by Nickel-Catalyzed C-N Borylation
The dimethylamino (Me2N) group is arguably the most versatile functional group capable of highly efficient and site-selective directed aromatic functionalizations at the ortho-, meta-, and para-positions depending on reaction conditions. While the repertoire of Me2N-directed reactions is growing at a rapid pace, the lack of a general method to transform this group to other functionalities hampers its wider application in organic synthesis. Here we report nickel-catalyzed C-N borylations of aryl- and benzyl-dimethylamines that permit the conversion of a huge library of largely underutilized Me2N-containing organic molecules into various functional molecules by taking advantage of the wealth of existing C-B functionalization methods.
Zhang, Hua,Hagihara, Shinya,Itami, Kenichiro
supporting information
p. 16796 - 16800
(2015/11/16)

Methanol-promoted borylation of arylamines: A simple and green synthetic method to arylboronic acids and arylboronates
A Sandmeyer borylation of arylamines via a SN2Ar pathway promoted by methanol with sodium nitrite and hydrochloric acid as diazotization agent has been developed, which provide a simple and green synthetic method to arylboronic acids and arylboronates. Georg Thieme Verlag Stuttgart New York.
Zhao, Cong-Jun,Xue, Dong,Jia, Zhi-Hui,Wang, Chao,Xiao, Jianliang
supporting information
p. 1577 - 1584
(2014/07/08)

Palladium-catalyzed borylation of aryl iodides with 2,3-dihydro-1H-benzo[d] [1,3,2]diazaboroles
The palladium-catalyzed borylation of aryl iodides with 2,3-dihydro-1H-benzo[d][1,3,2]diazaboroles was achieved. The mild reaction conditions employed allowed for the inclusion of a wide variety of functional groups in aryl iodides to be tolerated. Additionally, the borylated products can be transformed into the corresponding boronic acids or their esters under acidic conditions.
Murata, Miki,Hirai, Nobuyoshi,Okuyama, Michihiro,Namikoshi, Takeshi,Watanabe, Shinji
p. 193 - 199
(2014/01/17)

PREPARATION METHOD OF AROMATIC BORONATE COMPOUNDS
Preparation method of aromatic boronate compound is provided, in which the is as follows: reacting aromatic amine Ar-NH2, with diboronic ester and alkyl nitrite in the presence of organic solvent, where Ar represents non-heterocyclic aryl. It enables for the first time the preparation of aromatic boronate from aromatic amine in one step by the present method.
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(2012/07/28)

PREPARATION METHOD OF AROMATIC BORATE ESTER COMPOUND
Preparation method of aromatic boronate compound is provided, in which the step is as follows: reacting aromatic amine Ar-NH2, with diboronic ester and alkyl nitrite in the presence of organic solvent, where Ar represents non-heterocyclic aryl.
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(2012/08/08)

Anomalous reactivity of silylborane: Transition-metal-free boryl substitution of aryl, alkenyl, and alkyl halides with silylborane/alkoxy base systems
An unexpected borylation of organic halides with a silyborane in the presence of an alkoxy base has been observed. This formal nucleophilic boryl substitution can be applied to a broad range of substrates with high functional group compatibility. Even sterically hindered aryl bromides afforded the corresponding boryl compounds in high yields. Preliminary mechanistic studies indicated that this boryl substitution is promoted by neither transition-metal contamination nor a radical-mediated process.
Yamamoto, Eiji,Izumi, Kiyotaka,Horita, Yuko,Ito, Hajime
supporting information
p. 19997 - 20000
(2013/02/23)

Flow synthesis of arylboronic esters bearing electrophilic functional groups and space integration with Suzuki-Miyaura coupling without intentionally added base
We found that an integrated flow microreactor system enables the preparation of boronic esters bearing electrophilic functional groups using organolithium chemistry and that it allows for their use in Suzuki-Miyaura cross-coupling without intentionally added base. Based on this method, cross-coupling of two aryl halides bearing electrophilic functional groups was accomplished to obtain the corresponding biaryl compounds in one flow.
Nagaki, Aiichiro,Moriwaki, Yuya,Yoshida, Jun-Ichi
supporting information
p. 11211 - 11213
(2013/01/15)

Palladium-catalyzed borylation of aryl arenesulfonates with dialkoxyboranes
The cross-coupling of aryl arenesulfonates with dialkoxyboranes proceeded in the presence of Bu4NI and a catalytic amount of [Pd(dba) 2]/1,1'-bis(di-tert-butylphosphano)ferrocene, giving good yields of the corresponding arylboronates. The protocols tolerate a wide range of functional groups, including ester, nitrile, and ketone.
Murata, Miki,Oda, Takeshi,Sogabe, Yosuke,Tone, Hirofumi,Namikoshi, Takeshi,Watanabe, Shinji
p. 962 - 963
(2011/12/05)

Palladium-catalyzed borylation of aryl mesylates and tosylates and their applications in one-pot sequential suzuki-miyaura biaryl synthesis
Top of the one-pots! The first palladium-catalyzed borylation of aryl tosylates and mesylates is described. The reaction conditions are mild and provide excellent functional-group compatibility (e.g., R=CN, CHO, COOMe, C(O)R, NH2, or NH-indole; see scheme). Pd/MeO-CM-phos allows one-pot sequential reactions in the preparation of unsymmetrical biaryls. Copyright
Chow, Wing Kin,So, Chau Ming,Lau, Chak Po,Kwong, Fuk Yee
supporting information; experimental part
p. 6913 - 6917
(2011/08/03)

Synthesis and characterization of novel unnatural bichalcones
Five bichalcones (5-1 ～ 5-4, 9) were prepared by the reaction of biphenyl-4,4′-dicarbaldehyde (4) and 4,4′-dioxybenzaldehyde (8) with the respective acetophenone analogs via Claisen-Schmidt condensation and were then fully identified by 1H-NMR, 13C-NMR and mass analyses.
Gurung, Santosh K.,Kim, Soo Bae,Park, Haeil
p. 1919 - 1926
(2012/01/05)

Direct conversion of arylamines to pinacol boronates: A metal-free borylation process
Leave the metal out: Arylboronates are produced In moderate to good yields by direct borylation of readily available aryl amines (see scheme). The reaction can be carried out under air at room temperature and transition-metal catalysis is not required. The boronate products can be used without purification in SuzukiMiyaura cross-coupling reactions. Chemical equation representation
Mo, Fanyang,Jiang, Yubo,Qiu, Di,Zhang, Yan,Wang, Jianbo
supporting information; experimental part
p. 1846 - 1849
(2010/06/16)

Palladium- or nickel-catalyzed coupling reaction of dialkoxyboranes with chloroarenes: arylation of 1,3,2-dioxaborolanes or l,3,2-dioxaborinanes
The borylation of electron-deficient aryl chlorides with pinacolborane proceeded in the presence of BU4NI and a catalytic amount of Pd(dba)2 / bis(2-di-tert-butylphosphinophenyl) ether. The combination of NiCl2(dppp) catalyst and Bu4NBr was also efficient for the borylation of aryl chlorides.
Murata, Miki,Sambommatsu, Tomoko,Oda, Takeshi,Watanabe, Shinji,Masuda, Yuzuru
experimental part
p. 213 - 218
(2010/05/03)

A novel transmetallation of arylzinc species into arylboronates from aryl halides in a barbier procedure
A variety of functionalized arylboronates are obtained in moderate to excellent yield by a one-step chemical procedure from the corresponding halides and a haloboronic ester via an intermediate arylzinc species. The Royal Society of Chemistry.
Claudel, Stephanie,Gosmini, Corinne,Paris, Jean Marc,Perichon, Jacques
p. 3667 - 3669
(2008/03/14)

An efficient catalyst system for palladium-catalyzed borylation of aryl halides with pinacolborane
The combination of Pd(dba)2 and bis(2-di-tert-butyl- phosphinophenyl)ether has proven to be efficient for the cross-coupling of pinacolborane with aryl bromides and chlorides. The substrate scope is broad and the present system enables the synthesis of ortho-, meta-, and para-substituted electron-rich and -deficient arylboronates. Georg Thieme Verlag Stuttgart.
Murata, Miki,Sambommatsu, Tomoko,Watanabe, Shinji,Masuda, Yuzuru
p. 1867 - 1870
(2008/02/08)

Hydroboronation process
The invention relates to processes for the synthesis of aryl or alkene borates which comprises reacting: (i) an olefinic compound having a halogen or halogen-like substituent in a vinylic substitution position, or (ii) an aromatic ring having a halogen or halogen-like substituent in a ring substitution position, with a disubstituted monohydroborane in the presence of a Group 8-11 metal catalyst. The invention also relates to the use of these borates in coupling reactions. The invention further relates to certain disubstituted monohydroboranes and aryl or alkene borates.
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Page column 48-49

(2010/02/05)

FUROISOQUINOLINE DERIVATIVES, PROCESS FOR PRODUCING THE SAME AND USE THEREOF
A compound having a partial structure represented by Formula: or a salt thereof has an excellent phosphodiesterase (PDE) IV-inhibiting effect, and is useful as a prophylactic or therapeutic agent against inflammatory diseases, for example, bronchial asthma, chronic obstructive pulmonary disease (COPD), rheumatoid arthritis, autoimmune disease, diabetes and the like.
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(2008/06/13)

Benzofuran and dihydrobenzofuran derivatives useful as beta-3 adrenoreceptor agonists
This invention relates to novel benzofuran and dihydrobenzofuran compounds, pharmaceutical compositions containing such compounds, and methods of treating beta-3 adrenoreceptor-mediated conditions with such compositions.
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Page/Page column 34

(2010/01/31)

Steric and chelate directing effects in aromatic borylation [3]
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Cho,Iverson,Smith III
p. 12868 - 12869
(2007/10/03)

Palladium-catalyzed borylation of aryl halides or triflates with dialkoxyborane: A novel and facile synthetic route to arylboronates
A direct borylation of aryl halides or triflates with dialkoxyborane was investigated. The coupling reaction of pinacolborane with aryl halides or triflates in the presence of a catalytic amount of PdCl2(dppf) together with a base provided arylboronates in high yields. The product distributions were strongly dependent on the base employed, and the tertiary amine, especially Et3N, was effective for the selective formation of the boron-carbon bond. The reaction conditions were so mild that arylboronates having a variety of functional groups such as carbonyl, cyano, and nitro groups were readily prepared.
Murata, Miki,Oyama, Takashi,Watanabe, Shinji,Masuda, Yuzuru
p. 164 - 168
(2007/10/03)

Novel Palladium(0)-Catalyzed Coupling Reaction of Dialkoxyborane with Aryl Halides: Convenient Synthetic Route to Arylboronates
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Murata, Miki,Watanabe, Shinji,Masuda, Yuzuru
p. 6458 - 6459
(2007/10/03)