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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 13
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Original Articles

Palladium‐Catalyzed Enyne Cyclization of 2′‐Alkenyl 2‐Alkynoates in Imidazolium‐Type Ionic Liquids

Shaorong Yang College of Chemistry, South China University of Technology, Guangzhou, China
,
Huanfeng Jiang College of Chemistry, South China University of Technology, Guangzhou, ChinaCorrespondence[email protected]
,
Huoji Chen College of Chemistry, South China University of Technology, Guangzhou, China
,
Yanbin Xu College of Chemistry, South China University of Technology, Guangzhou, China
&
Wei Luo College of Chemistry, South China University of Technology, Guangzhou, China
Pages 2121-2129 | Received 07 Sep 2006, Published online: 03 Jul 2007
 
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Abstract

The use of [bmim][BF4], [bmim][PF6], and [bmim][Cl] ILs as the solvents in Pd(II)‐catalyzed enyne cyclization of 2′‐alkenyl 2‐alkynoates in the presence of cupric chloride has been investigated. The Z/E stereoselectivity of the reaction could range from 90:10 to 4:96 by tuning the amount of LiCl in ILs. After the separation of the product, the IL–catalyst mixture could be recovered by treatment with hydrochloric acid and recycled several times without an obvious loss of catalytic activity.

Acknowledgment

We are grateful to the National Natural Science Foundation of China (Grants 20625205, 20572027, and 20332030) and Youth Natural Science Foundation of South China University of Technology for financial support.

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