TEMPO-catalyzed C-N cross-coupling amidation of electron-deficient tertiary anilines

An efficient TEMPO-catalyzed C-N cross-coupling amidation of electron-deficient tertiary anilines was developed using N-haloamides. A variety of electron-deficient tertiary anilines and N-iodoamides or N-bromoamides reacted efficiently and provided the desired coupling products in high yields under milder conditions. Several control experiments were performed, and the results indicated that the reaction presumably involving an ionic mechanism was triggered by electrophilic activation and in situ generated oxoammonium salt (TEMPO+). [GRAPHICS] .

Automated summary

An efficient TEMPO-catalyzed C-N cross-coupling amidation reaction has been developed using N-haloamides, allowing for the synthesis of electron-deficient tertiary aniline derivatives under milder conditions.