Observations on the Deprotection of Pinanediol and Pinacol Boronate Esters via Fluorinated Intermediates
- 16 December 2009
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 75 (2), 468-471
- https://doi.org/10.1021/jo901930v
Abstract
Methods for the deprotection of pinanediol and pinacol esters of various boronic acids via fluoroborane intermediates were evaluated. Treatment of the boronate esters with potassium hydrogen difluoride normally gives trifluoroborate salts; in the case of α-amido alkyl or o-amido phenyl boronate esters, aqueous workup gives difluoroboranes. Procedures for transformation of both trifluoroborates and difluoroboranes to free boronic acids are described.Keywords
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