Mild and Rapid Hydroxylation of Aryl/Heteroaryl Boronic Acids and Boronate Esters with N-Oxides

Chen Zhu*, Rui Wang and J. R. Falck*

*Division of Chemistry, Department of Biochemistry, University of Texas Southwestern Medical Center, Dallas, Texas 75390, United States, Email: j.falckutsouthwestern.edu, chen.zhuutsouthwestern.edu

C. Zhu, R. Wang, J. R. Falck, Org. Lett., 2012, 14, 3494-3497.

DOI: 10.1021/ol301463c

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Abstract

Aryl and heteroaryl boronic acids and boronate esters are within minutes transformed into the corresponding phenols in the presence of N-oxides in an open flask at ambient temperature. This transformation tolerates a wide variety of functional groups.

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proposed mechanism

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Key Words

Phenols

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ID: J54-Y2012-2280