The efficient syntheses of aryl nitriles have gained much attention because of their synthetic potential for a variety of useful functionalities, and great importance in nature products, dyes, and biologically active compounds. In the past decades, extensive investigation has been made into cyanation reactions. Traditional synthetic approaches involve Sandmeyer reaction of aryldiazonium salts and Rosenmund–von Braun reaction of aryl halides with stoichiometric amount of CuCN salt. Recently, transition-metal catalyzed direct cyanation of aryl C−H bonds has emerged as a promising alternative. A number of transition metals have been proved to be effective catalysts with both metallic and organic CN surrogates. As a representative cyano source, N-cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS) is a bench-stable, environmentally benign, and readily available electrophilic cyanating agent. On the other hand, imidazopyridine scaffold is an important building block in synthetic chemistry, medicinal chemistry, and material chemistry. Based on our previous report and recent progress, we herein report the Rh-catalyzed C-H cyanation assisted by imidazopyridine group (Scheme 1).

Rh-catalyzed C-H cyanation of imidazopyridine using N-cyano-N-phenyl-p-methylbenzenesulfonamide as the cyano source

253rd National Meeting (2017)

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