Radical-mediated chemo-divergent recyclization of 1,2,3,4-benzothiatriazine-1,1-dioxides: alkyl migration and dearomatization

Abstract

A divergent denitrogenation/recyclization of 1,2,3,4-benzothiatriazine-1,1-dioxides is disclosed, including C(sp²)-alkyl transposition and aniline dearomatization. Regarding the alkyl migration process, a rare radical-mediated model is presented. Synthetically, sterically-congested biaryl sultams and ortho-all carbon quaternary stereocenter-substituted imines are expeditiously assembled in a simple reaction system. Mechanistic insights indicate that an innovative pattern of diradical-triggered addition probably plays an essential role in the process of C(sp²)-alkyl transformation.