Aerobic Oxidative C-H Olefination of Arylamides with Unactivated Olefins via a Rh(III)-Catalyzed C-H Activation

An efficient Rh(III)-catalyzed aerobic oxidative C-H alkenylation of arylamides with unactivated alkenes is described. The olefination reaction was compatible with various substituted arylamides including primary, secondary, and tertiary as well as functionalized unactivated olefins. Meanwhile, ortho mono/bisalkylated arylamides were synthesized in the reaction of arylamides with norbornene. In the alkenylation reaction, molecular oxygen along with organic acid was used to regenerate the active catalyst for the next catalytic cycle. A possible reaction mechanism involving CH activation/insertion/beta-hydride elimination followed by aerobic oxidation was proposed and supported by the deuterium labeling studies.

Automated summary

An efficient Rh(III)-catalyzed aerobic oxidative C-H alkenylation of arylamides with unactivated alkenes is described in this study. The reaction is compatible with various substituted arylamides and unactivated olefins, and can also synthesize ortho mono/bisalkylated arylamides under specific conditions. The proposed reaction mechanism involves CH activation/insertion/beta-hydride elimination followed by aerobic oxidation, supported by deuterium labeling studies.