Visible-light-driven C–H functionalization of double bonds with diazo compounds under mild reaction conditions

Abstract

Expanding the toolbox of C–H functionalization reactions applicable to the late-stage modification of complex molecules of interest in medicinal chemistry is a key strategy for drug development. Herein, we report an unusual visible-light-induced olefinic C(sp²)–H functionalization of olefins with diazo derivatives using an Ir(III) photocatalyst. The approach demonstrates the potential for targeting double bonds, such as those present in enol ethers, and has been further applied to 1,1-disubstituted alkenes. This efficient methodology affords unprecedented Heck-type products in good to excellent yields under mild conditions. Further derivatizations of the final products are shown to demonstrate the robustness of the methodology. The reaction pathway was validated through electrochemical and photophysical experiments as well as computational studies.