Seth C. Cowan, Courtney D. Glenn, Mason D. Hamilton, Anas Ansari, Matthew R. Ross, David W. Shelly, Brian V. Popp and Margaret J. Hilton*,
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Reactivity of Alcohol Substrates and Boron-Containing Complexes in C–H Alkylation Enabled by Photoredox, Hydrogen Atom Transfer, and Boronic Acid Catalysis
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.
期刊介绍:
Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.