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

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, Email: zpzhanxmu.edu.cn

Z.-P. Zhan, J.-L. Yu, Y.-Y. Cui, R.-F. Yang, W.-Z. Yang, J.-P. Li, J. Org. Chem., 2006, 71, 8298-8301.

DOI: 10.1021/jo061234p

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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, forms new C-C, C-O, C-S and C-N bonds.

see article for more examples

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Nucleophilic Substitution of Secondary Alkyl-Substituted Propargyl Acetates: An Economic and Practical Indium Trichloride Catalyzed Access

M. Lin, L. Hao, X.-t. Liu, Q.-z. Chen, F. Wu, P. Yan, S.-x. Xu, X.-l. Chen, J.-j. Wen, Z.-p. Zhan, Synlett, 2011, 665-670.

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Key Words

propargylic substitution, ethers, amines, sulfides

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ID: J42-Y2006-3370