Pd(OAc)2/DABCO as a Highly Active Catalytic System for the Heck Reaction

Jin-Heng Li; De-Ping Wang; Ye-Xiang Xie

doi:10.1055/s-2005-869980

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Synthesis 2005(13): 2193-2197
DOI: 10.1055/s-2005-869980

PAPER

Pd(OAc)₂/DABCO as a Highly Active Catalytic System for the Heck Reaction

Jin-Heng Li*, De-Ping Wang, Ye-Xiang Xie
Key Laboratory of Chemical Biology & Traditional Chinese Medicine Research, College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081, P. R. China
Fax: +86(731)8872260; e-Mail: jhli@hunnu.edu.cn;

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Publication History

Received 23 February 2005
Publication Date:
24 June 2005 (online)

Abstract
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Abstract

The combination of Pd(OAc)₂ and DABCO (triethylenediamine) was observed as an efficient catalytic system for the Heck cross-coupling reaction. In the presence of Pd(OAc)₂ and DABCO, a number of ArX (X = I, Br, and Cl) were coupled with olefins efficiently and selectively to afford the corresponding unsymmetric internal olefins in good to excellent yields. Furthermore, the Pd(OAc)₂/DABCO-catalyzed Heck cross-coupling reaction provided high TONs up to 1,000,000.

Key words

Pd(dba)₂/DABCO - Heck cross-coupling reaction - aryl halide - olefin - turnover number

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Three roles of TBAB might play in the reaction: (i)activation of Pd(0) species with the formation of anionic species;(ii) stabilization of low co-ordination Pd(0) species;(iii) phase-transfer catalyst for the inorganic base/solvent/substrates/product phases. See references 5h, 6b, and 9.