A novel method for the conversion of vinyl triflates into alpha-trifluoromethylated ketones in the absence of external trifluoromethyl sources is described. This process accomplishes an efficient migration of the trifluoromethyl group of the
triflate to the a-position in the ketone through a radical process. The reaction proceeds by the addition of a trifluoromethyl radical to the vinyl triflate and subsequent fragmentation of the trifluoromethane sulfonyl radical. Based on this reaction, a one-pot two-step procedure for the trifluoromethy- lation of ketones was developed. The method presented herein also allows the transfer of perfluoroalkyl groups from vinyl perfluoroalkane sulfonates, which are readily accessible from alkynes and perfluoroalkanesulfonic acids.
Kawamoto, T.; Sasaki, R.; Kamimura, A. Angew. Chem. Int. Ed. 2017, 56, 1342–1345.
Highlighted in Synfacts, 2017, 1. DOI: 10.1055/s-0036-1589791
