A general method for the direct α-arylation of nitriles with aryl chlorides

被引：140

作者：

You, JS ^{[1
]}

Verkade, JG ^{[1
]}

机构：

[1] Iowa State Univ, Dept Chem, Ames, IA 50011 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 41期

关键词：

alpha-arylation; homogeneous catalysis; nitriles; P ligands; palladium;

D O I：

10.1002/anie.200351954

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The long-standing challenge of developing a general method for the title methodology is met for a broad range of aryl chlorides through the use of bicyclic P(iBuNCH2CH2)3N (1) as a bulky electron-rich ligand for palladium (see scheme, dba = dibenzylideneacetone).

引用

收藏

页码：5051 / 5053

页数：3

相关论文

共 39 条

[1]

Abele S, 2000, EUR J ORG CHEM, V2000, P1

[2] Palladium-catalyzed arylation of malonates and cyanoesters using sterically hindered trialkyl- and ferrocenyldialkylphosphine ligands [J].

Beare, NA ;

Hartwig, JF .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (02) :541-555

[3] A NOVEL AND SELECTIVE CLASS OF AZABICYCLIC MUSCARINIC AGONISTS INCORPORATING AN N-METHOXY IMIDOYL HALIDE OR NITRILE FUNCTIONALITY [J].

BROMIDGE, SM ;

BROWN, F ;

CASSIDY, F ;

CLARK, MSG ;

DABBS, S ;

HAWKINS, J ;

LOUDON, JM ;

ORLEK, BS ;

RILEY, GJ .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1992, 2 (08) :791-796

[4]

Brunner H, 2000, EUR J ORG CHEM, V2000, P2119

[5] Control of stereochemistry in an intramolecular Diels-Alder reaction by the phenylsulfonyl group; an improved synthesis of pisiferol [J].

Bush, EJ ;

Jones, DW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (23) :3531-3536

[6] Preparation of tertiary benzylic nitriles from aryl fluorides [J].

Caron, S ;

Vazquez, E ;

Wojcik, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (04) :712-713

[7] ASYMMETRIC-SYNTHESIS OF BETA-LACTAMS - HIGHLY DIASTEREOSELECTIVE ALKYLATION OF CHIRAL 2-CYANO ESTERS [J].

CATIVIELA, C ;

DIAZDEVILLEGAS, MD ;

GALVEZ, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (09) :2497-2505

[8] SYNTHESIS AND PROPERTIES OF ENANTIOPURE BICYCLIC AMIDINES [J].

CONVERY, MA ;

DAVIS, AP ;

DUNNE, CJ ;

MACKINNON, JW .

TETRAHEDRON LETTERS, 1995, 36 (24) :4279-4282

[9] UV PHOTO-ELECTRON SPECTROSCOPIC INVESTIGATION OF SOME POLYCYCLIC GROUP 5A COMPOUNDS AND RELATED ACYCLIC SPECIES .1. FREE AND COORDINATED AMINOPHOSPHINES AND RELATED-COMPOUNDS [J].

COWLEY, AH ;

LATTMAN, M ;

STRICKLEN, PM ;

VERKADE, JG .

INORGANIC CHEMISTRY, 1982, 21 (02) :543-549

[10] Palladium-catalyzed α-arylation of carbonyl compounds and nitriles [J].

Culkin, DA ;

Hartwig, JF .

ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (04) :234-245

← 1 2 3 4 →