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Zinc(II) Catalyzed Conversion of Alkynes to Vinyl Triflates in the Presence of Silyl Triflates

Mohammed H. Al-huniti and Salvatore D. Lepore*

*Department of Chemistry, Florida Atlantic University, Boca Raton, Florida 33431-0991, United States, Email: sleporefau.edu

M. H. Al-huniti, S. D. Lepore, Org. Lett., 2014, 16, 4154-4157.

DOI: 10.1021/ol501852n  (free Supporting Information)


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Abstract

Triflate salts of several transition metal catalysts greatly faciliate the conversion of alkynes to their corresponding vinyl triflates. Products are formed in high regioselectivity under mild conditions most especially using Zn(OTf)2. Internal alkynes bearing an aryl substituent afford vinyl triflates with a modest preference for the Z-isomer. A mechanism explains the unique role of silicon in this system.

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Key Words

Enols, Carbonyl Compounds


ID: J54-Y2014