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Enhanced Reactivity for Aromatic Bromination via Halogen Bonding with Lactic Acid Derivatives

Sarah I. Baker, Mahshid Yaghoubi, Samantha L. Bidwell, Savannah L. Pierce, Hrant P. Hratchian and Ryan D. Baxter*

*Department of Chemistry and Biochemistry, University of California, 5200 N. Lake Road, Merced, California 95343, United States, Email:

S. I. Baker, M. Yaghoubi, S. L. Bidwell, S. L. Pierce, H. P. Hratchian, R. D. Baxter, J. Org. Chem., 2022, 87, 8492-8502.

DOI: 10.1021/acs.joc.2c00611


Mandelic acid catalyzes a highly regioselective aromatic bromination with N-bromosuccinimide (NBS) under aqueous conditions at room temperature. Computational results demonstrate that Lewis basic additives interact with NBS to increase the electropositive character of bromine prior to electrophilic transfer.

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proposed mechanism

Key Words

bromination, NBS, organocatalysis

ID: J42-Y2022