Peri-Selective Direct Acylmethylation and Amidation of Naphthalene Derivatives Using Iridium and Rhodium Catalysts

An iridium-catalyzed acylmethylation and a rhodium-catalyzed amidation of naphthalene derivatives are reported, adopting sulfoxonium ylides and dioxazolones as carbene and nitrene transfer agents, respectively. The use of SMe group as a directing group was key to ensure the peri-selective functionalization, and it can be easily removed or diversely transformed to other synthetically useful functionalities after the catalysis.

Automated summary

The study describes iridium-catalyzed acylmethylation and rhodium-catalyzed amidation of naphthalene derivatives using sulfoxonium ylides and dioxazolones as carbene and nitrene transfer agents. The use of an SMe group as a directing group is crucial for achieving peri-selective functionalization, which can be easily removed or transformed after the catalysis into other synthetically useful functionalities.