Synthesis of 2-chloro-1,1-difluoroallyl mesylates through novel rearrangement and CC bond formation by their Pd-catalyzed reaction with diethylzinc |
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Authors: | Akira Ando |
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Institution: | Faculty of Pharmaceutical Sciences, Setsunan University, Nagaotoge-cho, Hirakata, Osaka 573-0101, Japan |
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Abstract: | Treatment of 2-chloro-3,3-difluoroprop-2-en-1-ol derivatives (2) with methanesulfonyl chloride in the presence of a base did not give the expected esters but 2-chloro-1,1-difluoroprop-2-enyl methanesulfonates (4) through a novel 3,3] sigmatropic rearrangement. Reaction of 4 with diethylzinc in the presence of tetrakis(triphenylphosphine) palladium gave 1-alkyl- or 1-aryl-2-chloro-3-fluoropenta-1,3-dienes in moderate to good yields through a C C bond formation followed by dehydrofluorination. |
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Keywords: | [3 3] Sigmatropic rearrangement Methanesulfonate Fluorine C els-cdn C bond formation" target="_blank">com/sd/entities/sbnd" class="glyphImg">C bond formation Palladium Diethylzinc 3-Fluoropenta-1 3-diene |
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