Synthetic Utility of N-Benzoyloxyamides as an Alternative Precursor of Acylnitrenoids for gamma-Lactam Formation

Abstract

Described herein is the development of a new entry of acylnitrenoid precursors for gamma-lactam synthesis via an intramolecular C-H amidation reaction. Upon Ir catalysis, N-benzoyloxyamides serve as efficient substrates to afford 5-membered amides. Mechanistic studies revealed that the generation of a putative Ir-carbonylnitrenoid via N-O bond cleavage is facilitated by the chelation of countercations. This protocol offers a convenient and step-economic route to gamma-lactams starting from the corresponding carboxylic acids.