title: Efficient hydrolysis of organotrifluoroborates via silica gel and water.
abstract: A general, mild, and efficient method for the hydrolysis of organotrifluoroborates to unveil boronic acids using silica gel and H(2)O was developed. This method proved to be tolerant of a broad range of aryl-, heteroaryl-, alkenyl-, and alkyltrifluoroborates as well as structurally diverse aminomethylated organotrifluoroborates. As anticipated, electron-rich substrates provided the corresponding boronic acids more readily than electron-poor substrates, owing to the resonance-stabilized difluoroborane intermediate. The method developed was expanded further for the conversion of organotrifluoroborates to the corresponding boronate esters.
authors.affiliation: Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA. gmolandr@sas.upenn.edu
authors.forename: Gary A
authors.initials: GA
authors.lastname: Molander
authors.forename: Livia N
authors.initials: LN
authors.lastname: Cavalcanti
authors.forename: Belgin
authors.initials: B
authors.lastname: Canturk
authors.forename: Po-Shen
authors.initials: PS
authors.lastname: Pan
authors.forename: Lauren E
authors.initials: LE
authors.lastname: Kennedy
mesh_terms: D001881:Borates / Q000737:chemistry*; D005782:Gels / Q000737:chemistry*; D006868:Hydrolysis; D015394:Molecular Structure; D012822:Silicon Dioxide / Q000737:chemistry*; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry*
chemical_list: D001881:Borates; D005782:Gels; D014867:Water; D012822:Silicon Dioxide