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

25 March 2022, Version 2
This content is a preprint and has not undergone peer review at the time of posting.


Based on systematic electrochemical analysis, an integrated synthetic platform of C(sp3)-based organoboron com- pounds 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. Ultimately, a new di- mension in the activation strategies for organoboron compounds was accomplished through the electrochemically driven reaction development.


Organoboron compounds
SP3-hybridized carbon atom


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