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SO2F2-Mediated Oxidative Dehydrogenation and Dehydration of Alcohols to Alkynes
Gao-Feng Zha1, Wan-Yin Fang1, You-Gui Li2
1State Key Laboratory of Silicate Materials for Architectures, and School of Chemistry, Chemical Engineering and Life Sciences , Wuhan University of Technology , 205 Luoshi Road , Wuhan 430070 , P.R. China.
Abstract:
Direct synthesis of alkynes from inexpensive, abundant alcohols was achieved in high yields (greater than 40 examples, up to 95% yield) through a SO2F2-promoted dehydration and dehydrogenation process. This straightforward transformation of sp3-sp3 (C-C) bonds to sp-sp (C≡C) bonds requires only inexpensive and readily available reagents (no transition metals) under mild conditions. The crude alkynes are sufficiently free of impurities to permit direct use in further transformations, as illustrated by regioselective Huisgen alkyne-azide cycloaddition reactions with PhN3 to give 1,4-substituted 1,2,3-traiazoles (16 examples, up to 92% yield) and Sonogashira couplings (10 examples, up to 77% yield).
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