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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.

SUBMITTER: Molander GA

PROVIDER: S-EPMC2763364 | biostudies-literature | 2009 Oct

REPOSITORIES: biostudies-literature

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Efficient hydrolysis of organotrifluoroborates via silica gel and water.

Molander Gary A GA Cavalcanti Livia N LN Canturk Belgin B Pan Po-Shen PS Kennedy Lauren E LE

The Journal of organic chemistry 20091001 19

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 difluorob ...[more]

PMID: 19743828

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