Gold‐catalyzed C−H Functionalization of Phenothiazines with Aryldiazoacetates
Sripati Jana, Claire Empel, Chao Pei, Thành Vinh Nguyễn, René M. Koenigs
Abstract
Abstract Phenothiazine is an important structural motif in pharmaceuticals and advanced functional organic materials. However, the C−H functionalization reaction of N ‐protected phenothiazine is rather unexplored and often shadowed by its chemical reactivity on the heteroatomic centers, which limits the diversity of its potential applications. This report demonstrates a straightforward approach towards the site‐selective C−H functionalization of phenothiazine at the para ‐position of N atom via gold‐catalyzed carbene transfer reactions (37 examples, up to 83% yield). The mechanism behind the regionselectivity of the C−H functionalization reaction was also elucidated by a combination of computational and experimental studies. magnified image