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Efficient Hydrolysis of Organotrifluoroborates via Silica Gel and Water

2009; American Chemical Society; Volume: 74; Issue: 19 Linguagem: Inglês

10.1021/jo901441u

1520-6904

Gary A. Molander, Lívia N. Cavalcanti, Belgin Canturk, Po‐Shen Pan, Lauren E. Kennedy,

Chemical Synthesis and Reactions

A general, mild, and efficient method for the hydrolysis of organotrifluoroborates to unveil boronic acids using silica gel and H2O 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.