A Unified Synthetic Strategy to Introduce Heteroatoms via Electrochemical Functionalization of Alkyl Organoboron Reagents

Abstract

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