An electrophilic, imide-based, visible light-promoted photoredox/Ni cross-coupling reaction for the synthesis of aliphatic ketones has been developed. This protocol proceeds through amide N-C(O) bond activation, made possible through the lower activation energy for metal insertion into this bond owing to delocalization of the lone pair of electrons on the nitrogen by electron-withdrawing groups. The operationally simple and mild cross-coupling reaction is performed at ambient temperature and exhibits tolerance for a variety of functional groups. In this cross-coupling reaction, aliphatic ketones, α-amino ketones, and α-alkoxy ketones are obtained in one step from bench stable imides and potassium alkyltrifluoroborates as the coupling partners

Synthesis of aliphatic ketones <i>via</i> N-C bond cleavage of imides under photoredox/Ni dual catalysis

254th National Meeting (2017)

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Synthesis of aliphatic ketones via N-C bond cleavage of imides under photoredox/Ni dual catalysis