Regio- and stereoselective dimerization of terminal alkynes to enynes catalyzed by a palladium/imidazolium system

被引:100
作者
Yang, CL [1 ]
Nolan, SP [1 ]
机构
[1] Univ New Orleans, Dept Chem, New Orleans, LA 70148 USA
关键词
D O I
10.1021/jo010837s
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A Palladium/imidazolium chloride system has been used to mediate the dimerization of terminal alkynes to enynes. The combination of 1 mol % Pd(OAc)(2) and 2 mol % IMes.HCl in the presence Of CS2CO3 as base shows high activity and high regio- and steroselectivity for the dimerization of aryl and aliphatic terminal alkynes to enynes.
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页码:591 / 593
页数:3
相关论文
共 42 条
[1]  
ADUENGO AJ, 1998, CHEM Z, V32, P6
[2]  
Arduengo A. J., 1991, U. S. Patent, Patent No. [5,077,414, 5077414]
[3]   ELECTRONIC STABILIZATION OF NUCLEOPHILIC CARBENES [J].
ARDUENGO, AJ ;
DIAS, HVR ;
HARLOW, RL ;
KLINE, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (14) :5530-5534
[4]  
BARLUENGA J, 1993, ANGEW CHEM INT EDIT, V32, P893, DOI 10.1002/anie.199308931
[5]   A RU(II) ENYNYL COMPLEX MEDIATES THE CATALYTIC DIMERIZATION OF 1-ALKYNES TO Z-1,4-DISUBSTITUTED ENYNES [J].
BIANCHINI, C ;
PERUZZINI, M ;
ZANOBINI, F ;
FREDIANI, P ;
ALBINATI, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (14) :5453-5454
[6]   N-heterocyclic carbenes Part 26.: N-heterocyclic carbene complexes of palladium(0):: synthesis and application in the Suzuki cross-coupling reaction [J].
Böhm, VPW ;
Gstöttmayr, CWK ;
Weskamp, T ;
Herrmann, WA .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 595 (02) :186-190
[7]   Stable carbenes [J].
Bourissou, D ;
Guerret, O ;
Gabbaï, FP ;
Bertrand, G .
CHEMICAL REVIEWS, 2000, 100 (01) :39-91
[8]   Synthesis of trisubstituted alkenes via olefin cross-metathesis [J].
Chatterjee, AK ;
Grubbs, RH .
ORGANIC LETTERS, 1999, 1 (11) :1751-1753
[9]   Selective catalytic hydrodimerization of 1,3-butadiene by palladium compounds dissolved in ionic liquids [J].
Dullius, JEL ;
Suarez, PAZ ;
Einloft, S ;
de Souza, RF ;
Dupont, J ;
Fischer, J ;
De Cian, A .
ORGANOMETALLICS, 1998, 17 (05) :815-819
[10]   Amination reactions of aryl halides with nitrogen-containing reagents mediated by palladium/imidazolium salt systems [J].
Grasa, GA ;
Viciu, MS ;
Huang, JK ;
Nolan, SP .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (23) :7729-7737