Tandem Pd-Catalyzed Double C-C Bond Formation: Effect of Water

被引：133

作者：

Chai, David I. ^{[1
]}

Lautens, Mark ^{[1
]}

机构：

[1] Univ Toronto, Davenport Res Lab, Dept Chem, Toronto, ON M5S 3H6, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 08期

基金：

加拿大自然科学与工程研究理事会;

关键词：

CROSS-COUPLING REACTIONS; O REDUCTIVE ELIMINATION; DIELS-ALDER REACTION; DIRECT ARYLATION; STEREOSELECTIVE-SYNTHESIS; SELECTIVE SYNTHESIS; ANTIVIRAL ACTIVITY; ARYL HALIDES; PALLADIUM; FUNCTIONALIZATION;

D O I：

10.1021/jo900053b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A highly efficient water-accelerated palladium-catalyzed reaction of gem-dibromoolefins with a boronic acid via a tandem Suzuki-Miyaura coupling and direct arylation is reported. A wide range of aryl, alkenyl, and alkyl boronic acids, as well as a variety of substitution patterns on the phenyl ring, are tolerated. Additionally, mechanistic studies were conducted to ascertain the order of the couplings as well as the role(s) of water. Results from this study indicate that the major pathway is a Suzuki-Miyaura coupling/direct arylation sequence and that water accelerates the Pd(0) formation and Suzuki-Miyaura coupling.

引用

页码：3054 / 3061

页数：8

共 85 条

[1]

Ackermann L, 2007, TOP ORGANOMETAL CHEM, V24, P35, DOI 10.1007/3418_2007_062

[2] Domino N-H/C-H bond activation: Palladium-catalyzed synthesis of annulated heterocycles using dichloro(hetero)arenes [J].

Ackermann, Lutz ;

Althammer, Andreas .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (10) :1627-1629

[3] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].

Alberico, Dino ;

Scott, Mark E. ;

Lautens, Mark .

CHEMICAL REVIEWS, 2007, 107 (01) :174-238

[4]

Anastasia L.Negishi., 2002, Handbook of Organopalladium Chemistry for Organic Synthesis, V1, P311, DOI DOI 10.1002/0471212466.CH19

[5] Novel electron-rich bulky phosphine ligands facilitate the palladium-catalyzed preparation of diaryl ethers [J].

Aranyos, A ;

Old, DW ;

Kiyomori, A ;

Wolfe, JP ;

Sadighi, JP ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (18) :4369-4378

[6] Studies towards a postulated biomimetic Diels-Alder reaction for the synthesis of himgravine [J].

Baldwin, JE ;

Chesworth, R ;

Parker, JS ;

Russell, AT .

TETRAHEDRON LETTERS, 1995, 36 (52) :9551-9554

[7] 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

[8] 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

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

Batey, RA ;

Quach, TD .

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

[10] Palladium-catalyzed borylation of ortho-substituted phenyl halides and application to the one-pot synthesis of 2,2′-disubstituted biphenyls [J].

Baudoin, O ;

Guénard, D ;

Guéritte, F .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (26) :9268-9271

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