Modular construction of functionalized anilines via switchable C–H and N-alkylations of traceless N-nitroso anilines with olefins

Abstract

A switchable C–H alkylation and N-alkylation with great chemo- and site-selectivity enabled by N-nitroso anilines was developed, affording functionalized anilines, hydrazines and heterocycles. The exploration of strain-release as the key driving force with structurally diverse olefins enabled mild and practical sequential C–H and C–C or C–O cleavage. Notably, N-nitroso anilines could act as traceless directing groups to enable indole synthesis via dehydrogenative coupling with styrenes.