Organotrifluoroborates and Monocoordinated Palladium Complexes as Catalysts-A Perfect Combination for Suzuki-Miyaura Coupling

被引：388

作者：

Molander, Gary A. ^{[1
]}

Canturk, Belgin ^{[1
]}

机构：

[1] Univ Penn, Dept Chem, Philadelphia, PA 19104 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 49期

基金：

美国国家卫生研究院;

关键词：

cross-coupling; N-heterocycliccarbenes; organotrifluoroborates; phosphines; Suzuki-Miyaura coupling; HETEROCYCLIC CARBENE LIGANDS; HIGHLY EFFICIENT CATALYST; HETEROARYL BORONIC ACIDS; HINDERED ARYL CHLORIDES; GENERATED IN-SITU; OXIDATIVE-ADDITION; ARYLBORONIC ACIDS; CROSS-COUPLINGS; CARBON-CARBON; C-N;

D O I：

10.1002/anie.200904306

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Hitting the sweet spot: The combination of organotrifluoroborates and monocoordinated palladium complexes as catalysts in the Suzuki-Miyaura coupling reaction provides a powerful method for the creation of carbon-carbon bonds. The advantages of organotrifluoroborates include the numerous functional groups that are tolerated in the substrate, the mild reaction conditions, and the possibility to use different types of reagents. [Chemical Equation Presented]. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

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页码：9240 / 9261

页数：22

相关论文

共 192 条

[1] Directed ortho metalation-boronation and Suzuki-Miyaura cross coupling of pyridine derivatives:: A one-pot protocol to substituted azabiaryls [J].

Alessi, Manlio ;

Larkin, Andrew L. ;

Ogilvie, Kevin A. ;

Green, Laine A. ;

Lai, Sunny ;

Lopez, Simon ;

Snieckus, Victor .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (05) :1588-1594

[2] Non-conventional methodologies for transition-metal catalysed carbon-carbon coupling: a critical overview. Part 2: The Suzuki reaction [J].

Alonso, Francisco ;

Beletskaya, Irina P. ;

Yus, Miguel .

TETRAHEDRON, 2008, 64 (14) :3047-3101

[3] Sterically demanding, bioxazoline-derived N-heterocyclic carbene ligands with restricted flexibility for catalysis [J].

Altenhoff, G ;

Goddard, R ;

Lehmann, CW ;

Glorius, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15195-15201

[4] An N-heterocyclic carbene ligand with flexible steric bulk allows Suzuki cross-coupling of sterically hindered aryl chlorides at room temperature [J].

Altenhoff, G ;

Goddard, R ;

Lehmann, CW ;

Glorius, F .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (31) :3690-3693

[5]

Altenhoff G., 2003, Angew. Chem, V115, P3818, DOI [10.1002/ange.200351325, DOI 10.1002/ANGE.200351325]

[6] Identification of the effective palladium(0) catalytic species generated in situ from mixtures of Pd(dba)(2) and bidentate phosphine ligands. Determination of their rates and mechanism in oxidative addition [J].

Amatore, C ;

Broeker, G ;

Jutand, A ;

Khalil, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (22) :5176-5185

[7] Role of dba in the reactivity of palladium(0) complexes generated in situ from mixtures of Pd(dba)2 and phosphines [J].

Amatore, C ;

Jutand, A .

COORDINATION CHEMISTRY REVIEWS, 1998, 178 :511-528

[8]

[Anonymous], 2007, Top. Organomet. Chem, V21

[9] Suzuki-Miyaura cross-coupling of aryl and alkyl halides using palladium/imidazolium salt protocols [J].

Arentsen, K ;

Caddick, S ;

Geoffrey, F ;

Cloke, N ;

Herring, AP ;

Hitchcock, PB .

TETRAHEDRON LETTERS, 2004, 45 (17) :3511-3515

[10] 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

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