PALLADACYCLES AS EFFICIENT CATALYSTS FOR ARYL COUPLING REACTIONS

被引:422
作者
BELLER, M [1 ]
FISCHER, H [1 ]
HERRMANN, WA [1 ]
OFELE, K [1 ]
BROSSMER, C [1 ]
机构
[1] TECH UNIV MUNICH,INST ANORGAN CHEM,MUNICH,GERMANY
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1995年 / 34卷 / 17期
关键词
CATALYSIS; PALLADACYCLES; SUZUKI COUPLING;
D O I
10.1002/anie.199518481
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The catalytic CC coupling of chloroarenes by both the Heck and the Suzuki reactions has been achieved for the first time with new palladacycles of type 1, in which R can be, for instance, o‐tolyl or mesityl. They are an order of magnitude more active than conventional catalysts and, moreover, thermally considerably more robust. But above all, the cleavage of the PC bond and the deposition of palladium is not observed. Analogous reactions with bromoarenes can also be catalyzed to advantage with 1. The Heck reaction of haloarenes with vinyl derivatives (e.g., n‐butyl acryiate) gives (E)‐styrene derivatives in one step. In the Suzuki reaction the haloarenes are converted into biphenyl derivatives with phenylbornic acid, also in one step. (Figure Presented.) Copyright © 1995 by VCH Verlagsgesellschaft mbH, Germany
引用
收藏
页码:1848 / 1849
页数:2
相关论文
共 44 条
[11]   SELECTIVITY IN PALLADIUM CATALYZED ALLYLIC SUBSTITUTION [J].
FROST, CG ;
HOWARTH, J ;
WILLIAMS, JMJ .
TETRAHEDRON-ASYMMETRY, 1992, 3 (09) :1089-1122
[12]   MECHANISMS OF 1,1-REDUCTIVE ELIMINATION FROM PALLADIUM [J].
GILLIE, A ;
STILLE, JK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (15) :4933-4941
[13]  
Guram A. S., 1995, ANGEW CHEM, V107, P1456
[14]  
GURAM AS, 1995, ANGEW CHEM INT EDIT, V34, P1348, DOI 10.1002/anie.199513481
[15]  
Heck R.F., 1985, PALLADIUM REAGENTS O
[16]   PALLADIUM(II)-ASSISTED REACTIONS OF MONOOLEFINS [J].
HEGEDUS, LS .
TETRAHEDRON, 1984, 40 (13) :2415-2434
[17]  
Herrmann W. A., 1995, ANGEW CHEM, V107, P1989
[18]   MECHANISM OF THE HECK REACTION - CATALYST DEACTIVATION BY PC-BOND CLEAVAGE [J].
HERRMANN, WA ;
BROSSMER, C ;
OFELE, K ;
BELLER, M ;
FISCHER, H .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 491 (1-2) :C1-C4
[19]   PALLADACYCLES AS STRUCTURALLY DEFINED CATALYSTS FOR THE HECK OLEFINATION OF CHLOROARENES AND BROMOARENES [J].
HERRMANN, WA ;
BROSSMER, C ;
OFELE, K ;
REISINGER, CP ;
PRIERMEIER, T ;
BELLER, M ;
FISCHER, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (17) :1844-1848
[20]   TOPOGRAPHIC PROBES OF ANGIOTENSIN AND RECEPTOR - POTENT ANGIOTENSIN-II AGONIST CONTAINING DIPHENYLALANINE AND LONG-ACTING ANTAGONISTS CONTAINING BIPHENYLALANINE AND 2-INDAN AMINO-ACID IN POSITION 8 [J].
HSIEH, KH ;
LAHANN, TR ;
SPETH, RC .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (04) :898-903