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Palladium-Catalyzed Borylation of Primary Alkyl Bromides

Amruta Joshi-Pangu, Xinghua Ma, Mohamed Diane, Sidra Iqbal, Robert J. Kribs, Richard Huang, Chao-Yuan Wang and Mark R. Biscoe*

*Department of Chemistry, The City College of New York, 160 Convent Avenue, New York, New York 10031, United States, Email:

A. Joshi-Pangu, X. Ma, M. Diane, S. Iqbal, R. J. Kribs, R. Huang, C.-Y. Wang, M. R. Biscoe, J. Org. Chem., 2012, 77, 6629-6633.

DOI: 10.1021/jo301156e

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A mild Pd-catalyzed process for the borylation of primary alkyl bromides using bis(pinacolato)diboron as a boron source tolerates a wide range of functional groups on the alkyl bromide substrate and offers complete selectivity in the presence of a secondary bromide. This approach has been extended to the use of alkyl iodides and alkyl tosylates, as well as borylation reactions employing bis(neopentyl glycolato)diboron as the boron source.

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Key Words


ID: J42-Y2012-2550