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: rbaxter
ucmerced.edu
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
Abstract
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.
see article for more examples
proposed mechanism
Key Words
bromination, NBS, organocatalysis
ID: J42-Y2022
