Song Xiaoning, Chang Jian, Zhu Dongsheng, Li Jiaheng, Xu Cong, Liu Qun, Wang Mang
Department of Chemistry, Northeast Normal University, Renmin Street 5268, Changchun 130024, P. R. China.
Org Lett. 2015 Apr 3;17(7):1712-5. doi: 10.1021/acs.orglett.5b00488. Epub 2015 Mar 23.
A unique domino reaction of enolizable carbonyl compounds with Me3SiCF2Br to construct α-fluoroenones and α-fluoroenals is described to undergo the in situ formation of difluorocarbene and silyl enol ether, difluorocyclopropanation, desilylation, ring-opening, and defluorination sequence. In this tandem reaction, Me3SiCF2Br acts as not only the difluorocarbene source but also the TMS transfer agent as well as internal bromide and fluoride anion catalyst. It allows the transformations to occur smoothly under only a catalytic amount of n-Bu4NBr as initiator.
描述了一种烯醇化羰基化合物与Me3SiCF2Br的独特多米诺反应，用于构建α-氟代烯酮和α-氟代烯醛，该反应经历了二氟卡宾和硅烯醇醚的原位形成、二氟环丙烷化、脱硅、开环和脱氟序列。在这种串联反应中，Me3SiCF2Br不仅作为二氟卡宾源，还作为TMS转移剂以及内部溴化物和氟阴离子催化剂。它使得仅在催化量的n-Bu4NBr作为引发剂的情况下，转化反应就能顺利发生。
