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Electrooxidative Activation of B−B Bond in B<sub>2</sub>cat<sub>2</sub>: Access to <i>gem</i>‐Diborylalkanes via Paired Electrolysis

Bingbing Wang, Xiangyu Zhang, Yangmin Cao, Long Zou, Xiaotian Qi, Qingquan Lu

2023Angewandte Chemie International Edition42 citationsDOIOpen Access PDF

Abstract

Abstract This report describes the unprecedented electrooxidation of a solvent (e.g., DMF)‐ligated B 2 cat 2 complex, whereby a solvent‐stabilized boryl radical is formed via quasi‐homolytic cleavage of the B−B bond in a DMF‐ligated B 2 cat 2 radical cation. Cyclic voltammetry and density functional theory provide evidence to support this novel B−B bond activation strategy. Furthermore, a strategy for the electrochemical gem ‐diborylation of gem ‐bromides via paired electrolysis is developed for the first time, affording a range of versatile gem ‐diborylalkanes, which are widely used in synthetic society. Notably, this reaction approach is scalable, transition‐metal‐free, and requires no external activator.

Topics & Concepts

ElectrolysisChemistryBond cleavageHomolysisCyclic voltammetryElectrochemistrySolventTransition metalCombinatorial chemistryCatalysisElectrodePhysical chemistryRadicalOrganic chemistryElectrolyteRadical Photochemical ReactionsOrganoboron and organosilicon chemistrySulfur-Based Synthesis Techniques