Aryl Trifluoroborates in Suzuki-Miyaura Coupling: The Roles of Endogenous Aryl Boronic Acid and Fluoride

被引：178

作者：

Butters, Mike ^{[2
]}

Harvey, Jeremy N. ^{[1
]}

Jover, Jesus ^{[1
]}

Lennox, Alastair J. J. ^{[1
]}

Lloyd-Jones, Guy C. ^{[1
]}

Murray, Paul M. ^{[2
]}

机构：

[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England

[2] AstraZeneca, Bristol BS10 7ZE, Avon, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 30期

关键词：

boron; fluorides; homogeneous catalysis; palladium; reaction mechanisms; ELECTROPHILIC DISPLACEMENT REACTIONS; ARYLBORONIC ACIDS; POTASSIUM ARYL; ORGANOTRIFLUOROBORATE SALTS; PHOSPHINE COMPLEXES; ARENEBORONIC ACIDS; ALKENYL BROMIDES; PALLADIUM; REDUCTION; CATALYSTS;

D O I：

10.1002/anie.201001522

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Undercover agents: The biaryl coupling of an aryltrifluoroborate with an aryl bromide involves in situ hydrolysis of the boron reagent. The hydrolysis products are key components in ensuring that the reaction proceeds with high efficiency and avoids the extensive generation of undesired phenolic and homocoupling side products. (Chemical equation Presented). © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.

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收藏

页码：5156 / 5160

页数：5

相关论文

共 56 条

[1] Mechanism of the palladium-catalyzed homocoupling of arylboronic acids: Key involvement of a palladium peroxo complex [J].

Adamo, Carlo ;

Amatore, Christian ;

Ciofini, Ilaria ;

Jutand, Anny ;

Lakmini, Hakim .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6829-6836

[2]

[Anonymous], 2009, ANGEW

[3] Electrospray ionization mass spectrometry detection of intermediates in the palladium-catalyzed oxidative self-coupling of areneboronic acids [J].

Aramendía, MA ;

Lafont, F ;

Moreno-Mañas, M ;

Pleixats, R ;

Roglans, A .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (10) :3592-3594

[4] Improved method for the conversion of pinacolboronic esters into trifluoroborate salts: facile synthesis of chiral secondary and tertiary trifluoroborates [J].

Bagutski, Viktor ;

Ros, Abel ;

Aggarwal, Varinder K. .

TETRAHEDRON, 2009, 65 (48) :9956-9960

[5] Efficient catalyst for the Suzuki-Miyaura coupling of potassium aryl trifluoroborates with aryl chlorides [J].

Barder, TE ;

Buchwald, SL .

ORGANIC LETTERS, 2004, 6 (16) :2649-2652

[6] Synthesis and cross-coupling reactions of tetra alkylammonium organotrifluoroborate salts [J].

Batey, RA ;

Quach, TD .

TETRAHEDRON LETTERS, 2001, 42 (52) :9099-9103

[7] Palladium catalysts for the Suzuki cross-coupling reaction: An overview of recent advances [J].

Bellina, F ;

Carpita, A ;

Rossi, R .

SYNTHESIS-STUTTGART, 2004, (15) :2419-2440

[8] Direct evidence for base-mediated decomposition of alkyl hydroperoxides (ROOH) in the gas phase [J].

Blanksby, SJ ;

Ellison, GB ;

Bierbaum, VM ;

Kato, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (13) :3196-3197

[9] Asymmetric Rh(I)-Catalyzed Addition of MIDA Boronates to N-tert-Butanesulfinyl Aldimines: Development and Comparison to Trifluoroborates [J].

Brak, Katrien ;

Ellman, Jonathan A. .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (09) :3147-3150

[10] Potassium trifluoro(organo)borates: New perspectives in organic chemistry [J].

Darses, S ;

Genet, JP .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (22) :4313-4327

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