BiCl3-Catalyzed propargylic substitution reaction of propargylic alcohols with C-, O-, S- and N-centered nucleophiles

Zhuang-ping Zhan; Wen-zhen Yang; Rui-feng Yang; Jing-liang Yu; Jun-ping Li; Hui-juan Liu

doi:10.1039/B606470A

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BiCl₃-Catalyzed propargylic substitution reaction of propargylic alcohols with C-, O-, S- and N-centered nucleophiles†

Zhuang-ping Zhan,*^a Wen-zhen Yang,^a Rui-feng Yang,^a Jing-liang Yu,^a Jun-ping Li^a and Hui-juan Liu^a

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* Corresponding authors

^a Department of Chemistry and The Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian, P. R. China
E-mail: zpzhan@xmu.edu.cn
Fax: +86-592-2185780
Tel: +86-592-2180318

Abstract

A general and efficient BiCl₃-catalyzed substitution reaction of propargylic alcohols with carbon and heteroatom-centered nucleophiles such as allyl trimethylsilane, alcohols, aromatic compounds, thiols and amides, leading to the construction of C–C, C–O, C–S and C–N bonds, has been developed.

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Article information

DOI: https://doi.org/10.1039/B606470A
Article type: Communication
Submitted: 09 May 2006
Accepted: 12 Jun 2006
First published: 27 Jun 2006

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Chem. Commun., 2006, 3352-3354

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BiCl₃-Catalyzed propargylic substitution reaction of propargylic alcohols with C-, O-, S- and N-centered nucleophiles

Z. Zhan, W. Yang, R. Yang, J. Yu, J. Li and H. Liu, Chem. Commun., 2006, 3352 DOI: 10.1039/B606470A

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Chemical Communications