Nitrogenation of Amides via C-C and C-N Bond Cleavage

Amides are among the fundamental chemicals in organic chemistry. Compared to other carbonyl functional groups, the transformation of amide is relatively difficult and remains a challenge. The tra-ditional deconstruction transformations of amides to other functional products are usually limited to twisted or electronically activated amides. Herein, we describe a direct nitrogenation approach to con-vert amides into nitriles. This chemistry provides a novel amide transformation pathway via both C-C and C-N bond cleavage. Interestingly, the simple, readily available, and inexpensive inorganic salt NaNO2 is successfully employed as a nitrogen source in this organic N-incorporation process. Applications of this study are demonstrated through the late -stage modification of drug and natural product deri-vatives.