Carboamination and olefination: ortho C-H functionalization of phenoxyacetamide

Herein, we have demonstrated a rhodium-catalyzed carboamination of olefin with the double bond intact. For the first time, deacylative carboamination of the maleimide has been achieved wherein phenoxyacetamide has behaved as the aminating source. In addition to carboamination, we have also disclosed the C-H olefination protocol where the maleimide group has been installed successfully in the ortho-position of phenoxyacetamide. In this protocol, phenoxyacetamide behaved as a traceless directing group with the in situ release of acetamide. The base-assisted E2-elimination is the key to the success of the olefination reaction.

Automated summary

We have demonstrated a rhodium-catalyzed carboamination of olefin with the double bond intact. For the first time, deacylative carboamination of the maleimide has been achieved using phenoxyacetamide as the aminating source. We have also disclosed a C-H olefination protocol where the maleimide group is successfully installed in the ortho-position of phenoxyacetamide, utilizing phenoxyacetamide as a traceless directing group with in situ release of acetamide. Base-assisted E2-elimination plays a key role in the success of the olefination reaction.