Indium-Catalyzed Formal Carbon-Halogen Bond Insertion: Synthesis of α-Halo-α,α-disubstituted Esters from Benzylic Halides and Diazo Esters

One-carbon-unit insertion into carbon-halogen (C-X) bonds accompanied by the formation of a new C-X bond and carbon-chain elongation is a powerful synthetic method of complex organohalides. Herein, we developed an indium trihalide catalyzed formal insertion of diazo esters into a C-X (X = Cl, Br, I) bond. In the present system, the reactions of alpha-aryl diazo esters with benzylic chlorides, bromides, and iodides yielded alpha-chloro, alpha-bromo, and alpha-iodo esters, respectively.

Automated summary

This article describes a reaction method catalyzed by indium trihalide, which can insert diazo esters into carbon-halogen bonds, forming new carbon-halogen bonds and elongating the carbon chain.