Synthesis 2016; 48(01): 57-64
DOI: 10.1055/s-0035-1560348
paper
© Georg Thieme Verlag Stuttgart · New York

Ammonium Iodide Catalyzed Selenolactonization of Unsaturated Acids

Hongwei Shi
a   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310032, P. R. of China   Email: jieyan87@zjut.edu.cn
,
Chen Yu
a   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310032, P. R. of China   Email: jieyan87@zjut.edu.cn
,
Min Zhu
b   College of Biological and Environmental Sciences, Zhejiang Shuren University, Hangzhou 310015, P. R. of China
,
Jie Yan*
a   College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310032, P. R. of China   Email: jieyan87@zjut.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 26 June 2015

Accepted after revision: 05 September 2015

Publication Date:
24 September 2015 (online)


Abstract

A convenient procedure is developed for the preparation of selenolactones from unsaturated acids and diselenides using a catalytic amount of ammonium iodide in combination with m-chloroperoxybenzoic acid as the oxidant. This catalytic ring-closing method proceeds efficiently at room temperature under neutral conditions, and in short reaction times, to afford the corresponding selenolactones in good yields. Using the same reaction conditions, cyclic selenoethers and tellurocyclization products are prepared, thus extending the catalytic application of inorganic iodides in organic synthesis.

 
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