Photomediated controllable alkylation/nitrosoalkylation of N-heteroaromatics via nucleohomolytic substitution of alkylboronic esters with N-nitrosamines

Abstract

The development of sustainable late-stage functionalization (LSF) methods has become a focal point of research in the field of organic synthesis. Boronic acids and their derivatives are some of the most useful reagents and are suitable triggers for LSF. This study reports the production of diverse alkylated/nitrosoalkylated N-heteroaromatics via the photomediated nucleohomolytic substitution of alkylboronic esters with N-nitrosamines in the absence of a photocatalyst. This green approach facilitates LSF through various protodeboronation sequences for natural products and drug molecules, expanding the biologically relevant chemical space.