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Updated: Oct 10, 2025

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Homologation of Electron-Rich Benzyl Bromide Derivatives via Diazo C-C Bond Insertion
Atanu Modak1, Juan V Alegre-Requena2, Louis de Lescure2
1Department of Chemistry, University of Minnesota─Twin Cities, Minneapolis, Minnesota 55455, United States.
Abstract:
The ability to manipulate C-C bonds for selective chemical transformations is challenging and represents a growing area of research. Here, we report a formal insertion of diazo compounds into the "unactivated" C-C bond of benzyl bromide derivatives catalyzed by a simple Lewis acid. The homologation reaction proceeds via the intermediacy of a phenonium ion, and the products contain benzylic quaternary centers and an alkyl bromide amenable to further derivatization. Computational analysis provides critical insight into the reaction mechanism, in particular the key selectivity-determining step.
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