Me3SiCF2Br-Self-Assisted Domino Reaction: Catalytic Synthesis of α,α-Difluorocyclopentanones from Methylvinylketones.
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.
Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Faculty of Chemistry, Northeast Normal University , Changchun 130024, P. R. China.
Jian
J
Chang
Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Faculty of Chemistry, Northeast Normal University , Changchun 130024, P. R. China.
Cong
C
Xu
Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Faculty of Chemistry, Northeast Normal University , Changchun 130024, P. R. China.
Jie
J
Gao
Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Faculty of Chemistry, Northeast Normal University , Changchun 130024, P. R. China.
Fengyun
F
Gao
Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Faculty of Chemistry, Northeast Normal University , Changchun 130024, P. R. China.
Dongsheng
D
Zhu
Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Faculty of Chemistry, Northeast Normal University , Changchun 130024, P. R. China.|State Key Laboratory of Fine Chemicals, Dalian University of Technology , Dalian 116024, P. R. China.
Mang
0000-0001-8006-4626
M
Wang