Cobalt‐Catalyzed Carbonylation of <i>N</i>‐Alkylbenzaldimines to ‘<i>N</i>‐Alkylphthalimidines’ (= 2,3‐Dihydro‐1<i>H</i>‐isoindol‐1‐ones) <i>via</i> Tandem CH Activation and Cyclocarbonylation

Abstract

Abstract The reaction of N ‐alkylbenzaldimines with carbon monoxide (CO) in the presence of cobalt (Co) catalysts resulted in the formation of N ‐alkylphthalimidines ( Table 1 ). Their formation is proposed to occur by CH activation of the aryl ring, migratory insertion of the hydride species into the benzaldimine functionality, CO coordination, and insertion into the CoC bond, followed by reductive elimination of the N ‐alkylphthalimidine and regeneration of the starting Co species ( Scheme 4 ). Deuterium ( 2 H)‐labeling NMR studies are consistent with this mechanism ( Scheme 5 ).