Light-Driven Carbon-Carbon Coupling of α-sp3-CH of Aliphatic Alcohols with sp2-CH Bond of 1,4-Naphthoquinones

Here, an alpha-selective Csp3-H bond functionalization of primary aliphatic alcohols with 1,4-naphthoquinones yielded Csp2-Csp2 coupled products driven by blue-LED light under catalyst, metal, base, and reagent-free conditions. In this transformation, cleavage of three C-H bonds (two sp3-C-H, one sp2-C- H, and one O-H) and four new bonds formed, leading to fluorescent 2-acylated1,4-naphthohydroquinones.

Automated summary

This study achieved alpha-selective Csp3-H bond functionalization of primary aliphatic alcohols with 1,4-naphthoquinones, resulting in Csp2-Csp2 coupled products driven by blue-LED light under catalyst, metal, base, and reagent-free conditions. The transformation involved the cleavage of three C-H bonds (two sp3-C-H and one sp2-C-H) and one O-H bond, leading to the formation of fluorescent 2-acylated 1,4-naphthohydroquinones.