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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 2 , giving access to TMS-pinacol boronic ester products, was developed.

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