General Access to <i>C</i>-Centered Radicals: Combining a Bioinspired Photocatalyst with Boronic Acids in Aqueous Media.

ABSTRACT: Carbon-centered radicals are indispensable building blocks for modern synthetic chemistry. In recent years, visible light photoredox catalysis has become a promising avenue to access C-centered radicals from a broad array of latent functional groups, including boronic acids. Herein, we present an aqueous protocol wherein water features a starring role to help transform aliphatic, aromatic, and heteroaromatic boronic acids to C-centered radicals with a bioinspired flavin photocatalyst. These radicals are used to deliver a diverse pool of alkylated products, including three pharmaceutically relevant compounds, via open-shell conjugate addition to disparate Michael acceptors. The mechanism of the reaction is investigated by computational studies, deuterium labeling, radic

SUBMITTER: Chilamari M 

PROVIDER: S-EPMC12622572 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature