Application of palladacycles in Heck type reactions

被引:573
作者
Herrmann, WA
Böhm, VPW
Reisinger, CP
机构
[1] Tech Univ Munich, Inst Anorgan Chem, D-85747 Garching, Germany
[2] Bayer AG, Cent Res, D-47812 Krefeld, Germany
关键词
carbenes; catalysis; CC-coupling; CN-coupling; Heck reaction; palladacycles; palladium; phosphines;
D O I
10.1016/S0022-328X(98)01050-X
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
In the last 3 years, there have been tremendous developments in palladium catalytic systems for Heck type reactions. One of the successful approaches towards activation of less reactive substrates like aryl chlorides involves the use of palladacycles 1, 2 and 3 as catalyst precursors. This article describes the principles of these systems with an emphasis on our own work and features the ongoing literature discussion about possible mechanisms involving Pd(0)/Pd(II) or Pd(II)/Pd(IV) catalytic cycles for this class of catalyst. (C) 1999 Elsevier Science S.A. All rights reserved.
引用
收藏
页码:23 / 41
页数:19
相关论文
共 124 条
[71]   A short synthesis of the factor-Xa inhibitor DX-9065a using palladium-catalyzed key steps [J].
Kehr, C ;
Neidlein, R ;
Engh, RA ;
Brandstetter, H ;
Kucznierz, R ;
Leinert, H ;
Marzenell, K ;
Strein, K ;
vonderSaal, W .
HELVETICA CHIMICA ACTA, 1997, 80 (03) :892-896
[72]   PREPARATION OF CYCLOPENTADIENYL [O-(PHENYLAZO)PHENYL]NICKEL [J].
KLEIMAN, JP ;
DUBECK, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (10) :1544-&
[73]   SYNTHESIS OF INDENONES VIA PALLADIUM-CATALYZED ANNULATION OF INTERNAL ALKYNES [J].
LAROCK, RC ;
DOTY, MJ ;
CACCHI, S .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (17) :4579-4583
[74]   PALLADIUM-CATALYZED SYNTHESIS OF ARYLAMINES FROM ARYL HALIDES - MECHANISTIC STUDIES LEAD TO COUPLING IN THE ABSENCE OF TIN REAGENTS [J].
LOUIE, J ;
HARTWIG, JF .
TETRAHEDRON LETTERS, 1995, 36 (21) :3609-3612
[75]   A route to Pd-0 from Pd-II metallacycles in amination and cross-coupling chemistry [J].
Louie, J ;
Hartwig, JF .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1996, 35 (20) :2359-2361
[76]   PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOBORONIC ACIDS WITH ORGANIC ELECTROPHILES [J].
MARTIN, AR ;
YANG, YH .
ACTA CHEMICA SCANDINAVICA, 1993, 47 (03) :221-230
[77]   PALLADIUM-CATALYZED COUPLING OF TETRAORGANOTIN COMPOUNDS WITH ARYL AND BENZYL HALIDES - SYNTHETIC UTILITY AND MECHANISM [J].
MILSTEIN, D ;
STILLE, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (17) :4992-4998
[78]   PALLADIUM-CATALYZED SYNTHESES OF ARYL POLYENES [J].
MITSUDO, T ;
FISCHETTI, W ;
HECK, RF .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (09) :1640-1646
[79]   NEW STEREOSPECIFIC CROSS-COUPLING BY THE PALLADIUM-CATALYZED REACTION OF 1-ALKENYLBORANES WITH 1-ALKENYL OR 1-ALKYNYL HALIDES [J].
MIYAURA, N ;
YAMADA, K ;
SUZUKI, A .
TETRAHEDRON LETTERS, 1979, 20 (36) :3437-3440
[80]   ARYLATION OF OLEFIN WITH ARYL IODIDE CATALYZED BY PALLADIUM [J].
MIZOROKI, T ;
MORI, K ;
OZAKI, A .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1971, 44 (02) :581-+