Facile synthesis of substituted 1,1-difluoroallenes via carbonyl difluorovinylidenation

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Abstract

Two methods for the difluorovinylidenation of carbonyl compounds have been developed to synthesize 1,1-difluoroallenes bearing various substituents. The reaction of 1-bromo-2,2-difluorovinyllithium, generated from 1,1-dibromo-2,2-difluoroethylene and n-butyllithium, with aldehydes or ketones, and subsequent acetylation, gives 2-bromo-3,3-difluoroallylic acetates. Elimination of these acetates with n-butyllithium affords 1,1-difluoroallenes in high yield. 3,3-Difluoro-2-iodoallylic acetates are similarly prepared from aldehydes or ketones on treatment with 2,2-difluoro-1-iodovinyllithium, generated from 1,1,1-trifluoro-2-iodoethane and lithium diisopropylamide, followed by acetylation. These acetates readily undergo elimination with zinc metal to afford 1,1-difluoroallenes in high yield. © Georg Thieme Verlag Stuttgart · New York.

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Oh, K., Fuchibe, K., Yokota, M., & Ichikawa, J. (2012). Facile synthesis of substituted 1,1-difluoroallenes via carbonyl difluorovinylidenation. Synthesis, 44(6), 857–861. https://doi.org/10.1055/s-0031-1290157

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