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Unveiling the role of boroxines in metal-free carbon-carbon homologations using diazo compounds and boronic acids.

ABSTRACT: By means of computational and experimental mechanistic studies the fundamental role of boroxines in the reaction between diazo compounds and boronic acids was elucidated. Consequently, a selective metal-free carbon-carbon homologation of aryl and vinyl boroxines using TMSCHN2, giving access to TMS-pinacol boronic ester products, was developed.

SUBMITTER: Bomio C

PROVIDER: S-EPMC5859889 | biostudies-literature | 2017 Sep

REPOSITORIES: biostudies-literature

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Unveiling the role of boroxines in metal-free carbon-carbon homologations using diazo compounds and boronic acids.

Bomio Claudio C Kabeshov Mikhail A MA Lit Arthur R AR Lau Shing-Hing SH Ehlert Janna J Battilocchio Claudio C Ley Steven V SV

Chemical science 20170615 9

By means of computational and experimental mechanistic studies the fundamental role of boroxines in the reaction between diazo compounds and boronic acids was elucidated. Consequently, a selective metal-free carbon-carbon homologation of aryl and vinyl boroxines using TMSCHN<sub>2</sub>, giving access to TMS-pinacol boronic ester products, was developed. ...[more]

PMID: 29619197

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