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A General and Efficient FeCl₃-Catalyzed Nucleophilic Substitution of Propargylic Alcohols

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

Department of Chemistry and The Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, P. R. China zpzhan@xmu.edu.cn

J. Org. Chem., 2006, 71 (21), pp 8298–8301

DOI: 10.1021/jo061234p

Publication Date (Web): September 13, 2006

To whom correspondence should be addressed. Tel: +86(592) 2180318. Fax: +86(592) 2185780.

Abstract

A general and efficient FeCl₃-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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Published In Issue October 13, 2006
Received June 15, 2006

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A General and Efficient FeCl₃-Catalyzed Nucleophilic Substitution of Propargylic Alcohols