Oxidative C–H/N–H Carbonylation of Benzamide by Nickel Catalysis with CO as the Carbonyl Source

Abstract

An efficient and direct carbonylation of aminoquinoline benzamides has been developed using abundant and inexpensive Ni­(OAc)2·4H2O as the catalyst and carbon monoxide as a cost-efficient C1 building block. This process features good functional-group tolerance and can be conducted on gram scale. The directing group can be easily removed under mild conditions.

Recent Advances in Nickel Catalyzed Carbonylative Reactionsviathe Insertion of Carbon Monoxide†

“…In 2022, Ji and colleagues reported a carbonylation of aminoquinoline benzamides, as depicted in Scheme 7. [ 18 ] By employing Ni(OAc) 2 ·4H 2 O as the catalyst, they developed a direct and cost‐ effective method for carbonylation of benzamides using CO gas. This transformation demonstrates a high level of compatibility with diverse functional groups, leading to moderate yields of the desired products when substrates containing halogens, biphenyls, and polycyclic substituents are utilized.…”

Rhodium-catalysed additive-free carbonylation of benzamides with diethyl dicarbonate as a carbonyl source

“…Furthermore, these carbonylations with CO often necessitate oxidative reaction conditions, requiring expensive and toxic chemical oxidants like silver salts (Scheme 1B). [19][20][21][22][23][24] Alternatively, CO surrogates have emerged as an easy-to-handle C1 carbonyl source, addressing the challenges associated with the use of CO gas and facilitating a COfree phthalimide synthesis process. However, the utility of CO surrogates is still limited by the inclusion of stoichiometric additives such as a base and an oxidant (Scheme 1B).…”