Observations on the deprotection of pinanediol and pinacol boronate esters via fluorinated intermediates

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Abstract

(Chemical Equation Presented) 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. © 2009 American Chemical Society.

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Inglis, S. R., Woon, E. C. Y., Thompson, A. L., & Schofield, C. J. (2010). Observations on the deprotection of pinanediol and pinacol boronate esters via fluorinated intermediates. Journal of Organic Chemistry, 75(2), 468–471. https://doi.org/10.1021/jo901930v

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