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Reactivity of Alcohol Substrates and Boron-Containing Complexes in C-H Alkylation Enabled by Photoredox, Hydrogen
Seth C Cowan1, Courtney D Glenn1, Mason D Hamilton1
1C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, United States.
Abstract:
Using boronic acid, photoredox, and HAT catalysis, the relative alkylation reactivity of representative alkyl alcohols was evaluated through competition experiments, revealing higher initial reactivity for diols. Electron-poor arylboronic acid catalysts provide increased reaction efficiency for all substrates, which is attributed to a more dynamic and facile equilibrium between boron-containing species. Furthermore, β-carboxyboronic acids resulted in an additional increase in reaction efficiency, and the results from both catalyst classes were compared using kinetic profiles and a select scope of monoalcohols.
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