Efficient hydrolysis of organotrifluoroborates via silica gel and water.
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.
Molander
Gary A
GA
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA. gmolandr@sas.upenn.edu
Cavalcanti
Livia N
LN
Canturk
Belgin
B
Pan
Po-Shen
PS
Kennedy
Lauren E
LE
D001881:Borates / Q000737:chemistry*; D005782:Gels / Q000737:chemistry*; D006868:Hydrolysis; D015394:Molecular Structure; D012822:Silicon Dioxide / Q000737:chemistry*; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry*
D001881:Borates; D005782:Gels; D014867:Water; D012822:Silicon Dioxide