Synthesis of chiral N,N′-disubstituted 1,2-benzenediamines from o-dibromobenzene

被引：32

作者：

Rivas, FM ^{[1
]}

Riaz, U ^{[1
]}

Diver, ST ^{[1
]}

机构：

[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA

来源：

TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 08期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/S0957-4166(00)00124-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Palladium-catalyzed amination of o-dibromobenzene provided chiral N,N'-disubstituted 1,2-benzenediamines in good to excellent yields. The amination was executed stepwise and in one pot to give unsymmetrically and symmetrically substituted 1,2-benzenediamines. Incorporation of chiral primary amines was possible without racemization using catalytic Pd(2)dba(3)-BINAP. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：1703 / 1707

页数：5

相关论文

共 25 条

[1]

Beletskaya IP, 1999, SYNLETT, P1459

[2] Palladium-catalyzed amination of aryl dibromides with secondary amines: synthetic and mechanistic aspects [J].

Beletskaya, IP ;

Bessmertnykh, AG ;

Guilard, R .

TETRAHEDRON LETTERS, 1999, 40 (35) :6393-6397

[3] Palladium-catalyzed amination of dihalobenzenes [J].

Beletskaya, IP ;

Bessmertnykh, AG ;

Mishechkin, RA ;

Guilard, R .

RUSSIAN CHEMICAL BULLETIN, 1998, 47 (07) :1416-1417

[4] Recent synthetic advances in the nucleophilic amination of benzenes [J].

Belfield, AJ ;

Brown, GR ;

Foubister, AJ .

TETRAHEDRON, 1999, 55 (38) :11399-11428

[5] A second-generation catalyst for aryl halide amination: Mixed secondary amines from aryl halides and primary amines catalyzed by (DPPF)PdCl2 [J].

Driver, MS ;

Hartwig, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (30) :7217-7218

[6]

FROST CG, 1988, J CHEM SOC P1, P2615

[7] Palladium-catalyzed synthesis of pure, regiodefined polymeric triarylamines [J].

Goodson, FE ;

Hauck, SI ;

Hartwig, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (33) :7527-7539

[8] Regiodefined poly(N-arylaniline)s and donor-acceptor copolymers via palladium-mediated amination chemistry [J].

Goodson, FE ;

Hartwig, JF .

MACROMOLECULES, 1998, 31 (05) :1700-1703

[9]

GURAM AS, 1995, ANGEW CHEM INT EDIT, V34, P1348, DOI 10.1002/anie.199513481

[10] Sequential N-arylation of primary amines as a route to alkyldiarylamines [J].

Harris, MC ;

Geis, O ;

Buchwald, SL .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (16) :6019-6022