Copper-Mediated Selective Multiple Inert Chemical Bonds Cleavage for Cyanation of Indoles via Tandem Carbon and Nitrogen Atom Transfer

The activation of inert chemical bonds is an exciting area of research in chemistry because it enables the direct utilization of readily available starting materials and promotes atom- and step-economic synthesis. Undoubtedly, selectively activating and transforming multiple inert chemical bonds is an even more intriguing and demanding task in synthetic chemistry. However, due to its inherent complexity and extreme challenges, this endeavour is rarely accomplished. We report a copper-mediated complete cleavage and selective transformation of multiple inert chemical bonds of three easily available feedstocks, i.e., a sp2C-H bond in indoles, three sp3C-H bonds and one C-N bond in a methyl carbon atom in TMEDA, and the C equivalent to N triple bond in CH3CN. This reaction proceeds via tandem carbon and nitrogen atom transfer, and allows for the direct and efficient cyanation of indoles, presenting a simple and direct alternative for synthesizing 3-cyanoindoles. Selective activation and transformation of multiple inert chemical bonds is a challenging yet intriguing direction in synthetic chemistry. We report a copper-mediated complete cleavage and selective transformation of sp2C-H bond in indoles, three sp3C-H bonds and one C-N bond in a methyl carbon atom in TMEDA, and the C equivalent to N triple bond in CH3CN for cyanation of indoles via tandem carbon and nitrogen atom transfer. image