92838-85-2Relevant academic research and scientific papers
General access to C-centered radicals: Combining a bioinspired photocatalyst with boronic acids in aqueous media
Bloom, Steven,Chilamari, Maheshwerreddy,Immel, Jacob R.
, p. 12727 - 12737 (2020/11/18)
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, radical-trapping experiments, and spectroscopic analysis.
