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Published on: October 10, 2018
Electrochemical Activation of Bicyclo[1.1.0]butanes
Jeremy T Maddigan-Wyatt1, Daniil A Knyazev1, Daniel B Werz1
1Institute of Organic Chemistry, Albert-Ludwigs-Universität Freiburg, 79104 Freiburg, Germany.
Abstract:
Herein, we describe a novel, light, and catalyst-free electrochemical method for the activation of bicyclo[1.1.0]butanes (BCBs) enabling cycloaddition with aldehydes and arylation with arenes. This exceptionally mild strategy for BCB functionalization leverages preliminary anodic oxidation in concert with strain release to facilitate the formation of oxabicyclohexanes (oBCHs) and bis-arylated cyclobutane products. A plausible electrolytic mechanism is proposed, alongside insights garnered from mechanistic studies.
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