Transition-Metal-Catalyzed Reactions Involving Trifluoro Diazo Compounds and Their Surrogates

Fluorinated organic compounds represent an important and growing family of active ingredients in various fields, including material science, pharmaceutical chemistry and biological science. Developing efficient synthetic methods toward fluorinated organic compounds have attracted much attention. In recent years, transition-metal catalyzed reaction of trifluoro diazo compounds were a powerful and convenient approach to afford trifluoromethyl- and difluoromethyl-substituted compounds of value. In this review, the recent progress on transition-metal-catalyzed reactions involving trifluoro diazo compounds and their surrogates via trifluoromethylated transition-metal carbene complex is described in the sequence of 2,2,2-trifluorodiazoethane as carbene precursor, ethyl 3-trifluoro-2-diazo-propionate as carbene precursor, trifluoroethylamine hydrochloride or amines as the CF3CHN2 surrogate as well as trifluoro aldehydes/ketones N-sulfonylhydrazones as the trifluoro diazo compounds surrogate. Trifluoro diazo compounds were one kind of attractive building blocks with high reactivity. In recent years, transition-metal catalyzed reaction of trifluoro diazo compounds involving trifluoro diazo compounds and their surrogates was a powerful and convenient approach to synthesize trifluoromethyl- and difluoromethyl-substituted compounds, which are active ingredients in material science, pharmaceutical chemistry and biological science. In most cases, the key process of this type of transformations was the formation of transition-metal trifluoromethyl carbene species with the release of one molecular N2. Herein, we provide a comprehensive coverage of the recent progress in this field. image