A unified synthetic strategy to introduce heteroatoms via electrochemical functionalization of alkyl organoboron reagents

Abstract

Based on systematic electrochemical analyses, an integrated synthetic platform of C(sp3)-based organoboron compounds was established for the introduction of heteroatoms. The electrochemically mediated bond-forming strategy was shown to be highly effective for the functionalization of sp3-hybridized carbon atoms with significant steric hindrance. Moreover, virtually all the nonmetallic heteroatoms could be utilized as reaction partners using one unified protocol. The observed reactivity stems from the two consecutive single-electron oxidations of the substrate, which eventually generates an extremely reactive carbocation as the key intermediate. The detailed reaction profile could be elucidated through multifaceted electrochemical studies and the examination of the reaction kinetics. Ultimately, a new dimension in the activation strategies for organoboron compounds was accomplished through the electrochemically driven reaction development.

Revisiting Thin-Layer Electrochemistry in a Chip-Type Cell for the Study of Electroorganic Reactions

“…As an application, electrochemical formation of carbon-heteroatom bonds by carbocation pathway is demonstrated in our recent work. 66…”