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

Dedicated to Professor Shinji Murai for his great contribution to the chemistry of catalytic C–H bond activation.

Abstract

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.

Key words

C–H Activation - iridium - rhodium - alkylation - amidation

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