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

[11] Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure [J].

Barder, TE ;

Walker, SD ;

Martinelli, JR ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4685-4696

[12] Distinct mechanisms for the oxidative addition of chloro-, bromo-, and lodoarenes to a bisphosphine palladium(0) complex with hindered ligands [J].

Barrios-Landeros, F ;

Hartwig, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (19) :6944-6945

[13] Highly efficient monophosphine-based catalyst for the palladium-catalyzed Suzuki-Miyaura reaction of heteroaryl halides and heteroaryl boronic acids and esters [J].

Billingsley, Kelvin ;

Buchwald, Stephen L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (11) :3358-3366

[14] A new class of easily activated palladium precatalysts for facile C-N cross-coupling reactions and the low temperature oxidative addition of aryl chlorides [J].

Biscoe, Mark R. ;

Fors, Brett P. ;

Buchwald, Stephen L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (21) :6686-+

[15] Computational characterization of the role of the base in the Suzuki-Miyaura cross-coupling reaction [J].

Braga, AAC ;

Morgon, NH ;

Ujaque, G ;

Maseras, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (25) :9298-9307

[16] Atroposelective biaryl coupling with chiral catalysts: Total synthesis of the antileishmanial naphthylisoquinoline alkaloids ancistrotanzanine B and ancistroealaine A [J].

Bringmann, G ;

Hamm, A ;

Schraut, M .

ORGANIC LETTERS, 2003, 5 (16) :2805-2808

[17] PROTODEBORONATION OF THIOPHENBORONIC ACIDS [J].

BROWN, RD ;

BUCHANAN, AS ;

HUMFFRAY, AA .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1965, 18 (10) :1521-&

[18] Effects of ionic liquids on Pd-catalysed carbon-carbon bond formation [J].

Calo, Vincenzo ;

Nacci, Angelo ;

Monopoli, Antonio .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (17) :3791-3802

[19] Analysis of the reactions used for the preparation of drug candidate molecules [J].

Carey, John S. ;

Laffan, David ;

Thomson, Colin ;

Williams, Mike T. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (12) :2337-2347

[20]

Chahen L, 2003, SYNLETT, P1668

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