Shalini, Anand Gaurav, Neetu Malya, Ruchir Kant, Sathish Kumar Mudedla, Pintu Kumar Mandal
Site-selective C-H functionalization for constructing C-S bonds via thioglycosylation of aniline derivatives is highly desirable, as their distinctive properties enable applications across a wide range of fields. However, the execution of the same is challenging, due to the intrinsic electronic bias of aniline substrates. Accordingly, we present a metal-free, nondirected, and site-selective one-pot strategy for unprecedented regiodivergent C(sp2)-H thioglycosylation of anilines via quinone imine ketal intermediates. Mechanistic insights and the origin of regioselectivity were elucidated through control experiments, DFT studies, and single-crystal X-ray diffraction analysis.