Synthesis 2012; 44(17): 2707-2712
DOI: 10.1055/s-0032-1316753
paper
© Georg Thieme Verlag Stuttgart · New York

Benzyl-Type Cation Initiated Nucleophilic Substitution on Furan and Thiophene by Using α-EWG Ketene S,S-Acetals as Nucleophiles

Shaoguang Sun
a   Department of Chemistry, Northeast Normal University, Changchun, 130024, P. R. of China, Fax: +86(431)85099759   Email: liuj975@nenu.edu.cn   Email: wangm452@nenu.edu.cn
b   AstaTech (Chengdu) Pharmaceutical Co., Ltd, No. 488, Kelin West Road, Wenjiang District, Chengdu, 611137, P. R. of China
,
Jun Liu*
a   Department of Chemistry, Northeast Normal University, Changchun, 130024, P. R. of China, Fax: +86(431)85099759   Email: liuj975@nenu.edu.cn   Email: wangm452@nenu.edu.cn
,
Qun Liu
a   Department of Chemistry, Northeast Normal University, Changchun, 130024, P. R. of China, Fax: +86(431)85099759   Email: liuj975@nenu.edu.cn   Email: wangm452@nenu.edu.cn
,
Mang Wang*
a   Department of Chemistry, Northeast Normal University, Changchun, 130024, P. R. of China, Fax: +86(431)85099759   Email: liuj975@nenu.edu.cn   Email: wangm452@nenu.edu.cn
c   State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116012, P. R. of China
› Author Affiliations
Further Information

Publication History

Received: 27 April 2012

Accepted after revision: 26 June 2012

Publication Date:
03 August 2012 (online)


Abstract

An efficient method for introducing nucleophiles on furan and thiophene has been established via the in situ formation of benzyl-type carbocation, delocalization of the carbocation on heterocyclic ring, and nucleophilic trap of α-EWG ketene S,S-acetal sequence at the 5-position.

Supporting Information