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Observations on the Deprotection of Pinanediol and Pinacol Boronate Esters via Fluorinated Intermediates

Steven R Inglis, Esther C Y Woon, Amber L Thompson, Christopher J Schofield

J Org Chem. 2010 Jan 15;75(2):468-71.

PMID: 20014787

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 alpha-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.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
LS7931465 Potassium [4-(diethylamine-1-carbonyl)phenyl]trifluoroborate Potassium [4-(diethylamine-1-carbonyl)phenyl]trifluoroborate Price
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