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Catalyst- and solvent-free ipso-hydroxylation of arylboronic acids to phenols.

ABSTRACT: A catalyst-free method for the hydroxylation of arylboronic acids to form the corresponding phenols with sodium perborate as the oxidant was developed using water as the solvent. Under the reaction conditions, the yield of phenol reached 92% at only 5 min. Moreover, the reaction could be conducted without a catalyst under the solvent-free condition, the efficiency of which was as high as that of a liquid-phase reaction. Using a microcalorimeter, the reaction was found to be an exothermic reaction. The reaction mechanism was investigated and understood via DFT calculations, which revealed that it was a nucleophilic reaction.

SUBMITTER: Yang X

PROVIDER: S-EPMC9074145 | biostudies-literature | 2019 Oct

REPOSITORIES: biostudies-literature

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Catalyst- and solvent-free ipso-hydroxylation of arylboronic acids to phenols.

Yang Xiufang X Jiang Xulu X Wang Weitao W Yang Qi Q Ma Yangmin Y Wang Kuan K

RSC advances 20191025 59

A catalyst-free method for the hydroxylation of arylboronic acids to form the corresponding phenols with sodium perborate as the oxidant was developed using water as the solvent. Under the reaction conditions, the yield of phenol reached 92% at only 5 min. Moreover, the reaction could be conducted without a catalyst under the solvent-free condition, the efficiency of which was as high as that of a liquid-phase reaction. Using a microcalorimeter, the reaction was found to be an exothermic reactio ...[more]

PMID: 35529971

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