Journal
TETRAHEDRON LETTERS
Volume 57, Issue 23, Pages 2506-2510Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2016.04.099
Keywords
Oxidation; Arylboronic acid; Phenols; Urea-hydrogen peroxide
Categories
Funding
- IIT (BHU)
- DST - India [YSS/2014/000236]
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An efficient and practical method for the chemoselective ipso-hydroxylation of arylboronic acids is demonstrated using urea-hydrogen peroxide under catalyst free condition at room temperature. Remarkably, oxidation sensitive functional groups such as olefin, aldehyde, alcohol, ketone, and sulfide as well as heterocycles such as pyridine and thiophene were tolerated under the standard reaction condition. In addition to the solution phase, a solid phase ipso-hydroxylation of arylboronic acids has been investigated with urea hydrogen peroxide. The scope and limitations of the solid phase protocol is discussed. (C) 2016 Elsevier Ltd. All rights reserved.
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