Observations on the deprotection of pinanediol and pinacol boronate esters via fluorinated intermediates.
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.
Inglis
Steven R
SR
The Department of Chemistry, Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, OX1 3TA, United Kingdom.
Woon
Esther C Y
EC
Thompson
Amber L
AL
Schofield
Christopher J
CJ
D001880:Boranes / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D003500:Cyclization; D004952:Esters; D015394:Molecular Structure; D013237:Stereoisomerism
D001880:Boranes; D001897:Boronic Acids; D004952:Esters