A highly active palladium catalyst system for the arylation of anilines

被引:114
作者
Sadighi, JP [1 ]
Harris, MC [1 ]
Buchwald, SL [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
基金
美国国家科学基金会;
关键词
D O I
10.1016/S0040-4039(98)00988-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The chelating ligand bis[2-(diphenylphosphino)phenyl] ether (DPEphos), in combination with palladium acetate, forms a highly active catalyst system for the coupling of anilines with aryl bromides. The bisphosphine is easily prepared in large quantity and at low cost by a known procedure. The catalyst system is effective in coupling reactions involving a variety of substrates, including electron-poor anilines or electron-rich aryl bromides. In addition, it tolerates a high degree of steric congestion at both the aniline and the aryl bromide. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5327 / 5330
页数:4
相关论文
共 18 条
[1]   An improved method for the palladium-catalyzed amination of aryl triflates [J].
Ahman, J ;
Buchwald, SL .
TETRAHEDRON LETTERS, 1997, 38 (36) :6363-6366
[2]   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
[3]   Systematic variation of bidentate ligands used in aryl halide amination. Unexpected effects of steric, electronic, and geometric perturbations [J].
Hamann, BC ;
Hartwig, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (15) :3694-3703
[4]   NEW DIPHOSPHINE LIGANDS BASED ON HETEROCYCLIC AROMATICS INDUCING VERY HIGH REGIOSELECTIVITY IN RHODIUM-CATALYZED HYDROFORMYLATION - EFFECT OF THE BITE ANGLE [J].
KRANENBURG, M ;
VANDERBURGT, YEM ;
KAMER, PCJ ;
VANLEEUWEN, PWNM ;
GOUBITZ, K ;
FRAANJE, J .
ORGANOMETALLICS, 1995, 14 (06) :3081-3089
[5]   Palladium(0)-tetracyanoethylene complexes of diphosphines and a dipyridine with large bite angles, and their crystal structures [J].
Kranenburg, M ;
Delis, JGP ;
Kamer, PCJ ;
vanLeeuwen, PWNM ;
Vrieze, K ;
Veldman, N ;
Spek, AL ;
Goubitz, K ;
Fraanje, J .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1997, (11) :1839-1849
[6]   Discrete high molecular weight triarylamine dendrimers prepared by palladium-catalyzed amination [J].
Louie, J ;
Hartwig, JF ;
Fry, AJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (48) :11695-11696
[7]   Palladium-catalyzed amination of aryl triflates and importance of triflate addition rate [J].
Louie, J ;
Driver, MS ;
Hamann, BC ;
Hartwig, JF .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (05) :1268-1273
[8]   Palladium-catalyzed C-N(sp2) bond formation:: N-arylation of aromatic and unsaturated nitrogen and the reductive elimination chemistry of palladium azolyl and methyleneamido complexes [J].
Mann, G ;
Hartwig, JF ;
Driver, MS ;
Fernández-Rivas, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (04) :827-828
[9]   A general synthesis of end-functionalized oligoanilines via palladium-catalyzed amination [J].
Singer, RA ;
Sadighi, JP ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (01) :213-214
[10]   ACID-PROMOTED AROMATIC SUBSTITUTION PROCESSES IN PHOTOCHEMICAL AND THERMAL DECOMPOSITIONS OF ARYL AZIDES [J].
SUNDBERG, RJ ;
SLOAN, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (11) :2052-2057