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

Min Lin, Lu Hao, Xiao-tao Liu, Qing-zhen Chen, Feng Wu, Ping Yan, Su-xia Xu, Xin-liang Chen, Jia-jie Wen, Zhuang-ping Zhan*

*Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian, P. R. of China, Email: zpzhanxmu.edu.cn

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.

DOI: 10.1055/s-0030-1259557

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Abstract

An economic and practical transformation from secondary alkyl-substituted propargyl acetates to a variety of nucleophilic substitution products is catalyzed by inexpensive InCl₃. High yields and excellent chemoselectivity were obtained. Five-, six-, and seven-membered propargyl cycloethers were also successfully constructed.

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

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.

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Key Words

propargyl acetate, nucleophilic substitution, indium, propargyl cycloether, propargylic amines, sulfonamides, ethers, sulfides

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ID: J60-Y2011-0700