Efficient palladium-catalyzed coupling of aryl chlorides and tosylates with terminal alkynes: Use of a copper cocatalyst inhibits the reaction

被引：359

作者：

Gelman, D ^{[1
]}

Buchwald, SL ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 48期

关键词：

alkynes; aryl chlorides; C-C coupling; cross-coupling; palladium;

D O I：

10.1002/anie.200353015

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Less catalyst, lower temperature, and greater generality are the advantages of the new general protocol over those previously described for the palladium-catalyzed coupling of aryl chlorides and alkynes (see scheme). Better results are obtained without a copper cocatalyst, which has been found to inhibit product formation in the coupling reaction of aryl chlorides with terminal alkynes.

引用

页码：5993 / 5996

页数：4

共 26 条

[1] Oxime palladacycles:: Stable and efficient catalysts for carbon-carbon coupling reactions
Alonso, DA
Nájera, C
Pacheco, MC
[J]. ORGANIC LETTERS, 2000, 2 (13) : 1823 - 1826
[2] A copper- and amine-free Sonogashira-type coupling procedure catalyzed by oxime palladacycles
Alonso, DA
Nájera, C
Pacheco, MC
[J]. TETRAHEDRON LETTERS, 2002, 43 (51) : 9365 - 9368
[3] Böhm VPW, 2000, EUR J ORG CHEM, V2000, P3679, DOI 10.1002/1099-0690(200011)2000:22<3679::AID-EJOC3679>3.0.CO
[4] 2-X
[5] Brandsma L., 1998, APPL TRANSITION META, P179
[6] Layered double hydroxide supported nanopalladium catalyst for Heck-, Suzuki-, Sonogashira-, and Stille-type coupling reactions of chloroarenes
Choudary, BM
Madhi, S
Chowdari, NS
Kantam, ML
Sreedhar, B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (47) : 14127 - 14136
[7] Investigations into the Pd-catalysed cross-coupling of phenylacetylene with aryl chlorides:: simple one-pot procedure and the effect of ZnCl2 co-catalysis
Eberhard, MR
Wang, ZH
Jensen, CM
[J]. CHEMICAL COMMUNICATIONS, 2002, (08) : 818 - 819
[8] Alkynyl germatranes as alternative reagents for the preparation of biarylethynes
Faller, JW
Kultyshev, RG
Parr, J
[J]. TETRAHEDRON LETTERS, 2003, 44 (03) : 451 - 453
[9] A copper-free palladium catalyzed cross coupling reaction of vinyl tosylates with terminal acetylenes
Fu, XY
Zhang, SY
Yin, JG
Schumacher, DP
[J]. TETRAHEDRON LETTERS, 2002, 43 (37) : 6673 - 6676
[10] A copper-free Sonogashira coupling reaction in ionic liquids and its application to a microflow system for efficient catalyst recycling
Fukuyama, T
Shinmen, M
Nishitani, S
Sato, M
Ryu, I
[J]. ORGANIC LETTERS, 2002, 4 (10) : 1691 - 1694

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