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

Abstract

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 sp ²C–H bond in indoles, three sp ³C–H bonds and one C–N bond in a methyl carbon atom in TMEDA, and the C≡N triple bond in CH ₃CN. 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.

Keywords

Multiple inert chemical bonds / Bond cleavage / Carbon and nitrogen atom transfer / Cleavage reactions / Oxidation / Copper / Cyanation / Indole / Selectivity

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2024 SIOC, CAS, Shanghai, & WILEY-VCH GmbH.