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.
Org Lett. 2017 Apr 7;19(7):1850-1853. doi: 10.1021/acs.orglett.7b00611. Epub 2017 Mar 23.
A complete self-assistance strategy based on MeSiCFBr was used in the domino conversion of methylvinylketones into α,α-difluorinated cyclopentanones. Initiated by 5 mol % of nBuNBr, 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 MeSiCFBr as the difluorocarbene source, a silicon-based transfer agent, and a bromine anion releaser.
一个完全基于 MeSiCFBr 的自辅助策略被用于将甲基乙烯基酮转化为α,α-二氟环戊酮的多米诺转化中。在 5 mol % nBuNBr 的引发下，多步反应在温和条件下一锅进行，通过原位形成硅基二烯醇醚、二氟环丙烷化、热乙烯基环丙烷-环戊烯重排和脱硅反应来实现。该过程利用了 MeSiCFBr 作为二氟卡宾源、硅基转移试剂和溴阴离子释放剂的多重任务能力。
