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