Organophotoredox-Catalyzed Three-Component Coupling of Heteroatom Nucleophiles, Alkenes, and Aliphatic Redox Active Esters.

Affiliation

Shibutani S(1), Nagao K(1), Ohmiya H(1)(2).
Author information:
(1)Division of Pharmaceutical Sciences, Graduate School of Medical Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan.
(2)JST, PRESTO, 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan.

Abstract

This manuscript describes a visible-light-mediated organophotoredox catalytic process for vicinal difunctionalization of alkenes using heteroatom nucleophiles and aliphatic redox active esters. A wide range of heteroatom nucleophiles including alcohols, water, carboxylic acids, amides, and halogens can be used for this reaction. This radical relay type reaction allows forging of C(sp3)-C(sp3) with a carbon-centered radical and C(sp3)-heteroatom bonds with a benzyl cation on the vinylarenes with complete regioselectivity in a single step.