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PIFA-Mediated Esterification Reaction of Alkynes with Alcohols via Oxidative Cleavage of Carbon Triple Bonds

Qing Jiang, An Zhao, Bin Xu, Jing Jia, Xin Liu and Cancheng Guo*

*College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China, Email:

Q. Jiang, A. Zhao, B. Xu, J. Jia, X. Liu, C. Guo, J. Org. Chem., 2014, 79, 2709-2715.

DOI: 10.1021/jo5003517

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A metal-free esterification of a broad range of alkynes with alcohols in the presence of phenyliodine bis(trifluoroacetate) produces esters in good yields via carbon triple bond cleavage. The transformation proceeds via hydroxyethanones and ethanediones as intermediates and exhibits a broad substrate scope and good functional group tolerance.

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Key Words

esters, cleavage of alkynes, iodosobenzene bis(trifluoroacetate)

ID: J42-Y2014