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Issue 9, 2017
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Unveiling the role of boroxines in metal-free carbon–carbon homologations using diazo compounds and boronic acids

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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.

Graphical abstract: Unveiling the role of boroxines in metal-free carbon–carbon homologations using diazo compounds and boronic acids

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Article information


Submitted
19 May 2017
Accepted
15 Jun 2017
First published
15 Jun 2017

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2017,8, 6071-6075
Article type
Edge Article

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

C. Bomio, M. A. Kabeshov, A. R. Lit, S. Lau, J. Ehlert, C. Battilocchio and S. V. Ley, Chem. Sci., 2017, 8, 6071
DOI: 10.1039/C7SC02264F

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