Abstract
A complete self-assistance strategy based on Me3SiCF2Br was used in the domino conversion of methylvinylketones into α,α-difluorinated cyclopentanones. Initiated by 5 mol % of nBu4NBr, the multistep reaction occurred in one pot under mild conditions via the in situ formation of silyl dienol ethers, difluorocyclopropanation, thermal vinylcyclopropane-cyclopentene rearrangement, and desilylation. The process takes advantage of the multitasking capability of Me3SiCF2Br as the difluorocarbene source, a silicon-based transfer agent, and a bromine anion releaser.
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