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Construction of β‑Quaternary α,α-Difluoroketones via Catalytic Nucleophilic Substitution of Tertiary Alcohols with Difluoroenoxysilanes

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journal contribution
posted on 13.10.2020, 20:30 by Yong-Jia Hao, Yi Gong, Ying Zhou, Jian Zhou, Jin-Sheng Yu
An efficient Fe­(OTf)3-catalyzed nucleophilic substitution of cyclic or acyclic tertiary alcohols with difluoroenoxysilanes is developed, which provides a facile protocol for assembling structurally diverse α,α-gem-difluoroketones featuring a quaternary carbon center in good to excellent yields under mild conditions. Moreover, the diverse product elaborations highlight the utility of this protocol, as exemplified by the preparation of valuable difluorinated tricyclic indolines.