3 years ago

Synergistic Visible-Light Photoredox/Nickel-Catalyzed Synthesis of Aliphatic Ketones via N–C Cleavage of Imides

Synergistic Visible-Light Photoredox/Nickel-Catalyzed Synthesis of Aliphatic Ketones via N–C Cleavage of Imides
Javad Amani, Rauful Alam, Shorouk Badir, Gary A. Molander
An electrophilic, imide-based, visible-light-promoted photoredox/Ni-catalyzed cross-coupling reaction for the synthesis of aliphatic ketones has been developed. This protocol proceeds through N–C(O) bond activation, made possible through the lower activation energy for metal insertion into this bond due 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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00989

DOI: 10.1021/acs.orglett.7b00989

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