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Scope and Mechanism of a True Organocatalytic Beckmann Rearrangement with a Boronic Acid/Perfluoropinacol System under Ambient Conditions

Xiaobin Mo, Timothy D. R. Morgan, Hwee Ting Ang and Dennis G. Hall*

*Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada, Email:

X. Mo, T. D. R. Morgan, H. T. Ang, D. G. Hall, J. Am. Chem. Soc., 2018, 140, 5264-5271.

DOI: 10.1021/jacs.8b01618


2-Alkoxycarbonyl- and 2-phenoxycarbonyl-phenylboronic acid are efficient catalysts for the direct and chemoselective activation of oxime N-OH bonds in the Beckmann rearrangement. Using only 5 mol % of boronic acid catalyst and perfluoropinacol as an additive in a polar solvent mixture, the operationally simple protocol features mild conditions, a broad substrate scope, and a high functional group tolerance.

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Key Words

Beckmann Rearrangement, Organocatalysis

ID: J48-Y2018