Toward a Unified Mechanism for Oxoammonium Salt-Mediated Oxidation Reactions: A Theoretical and Experimental Study Using a Hydride Transfer Model

Overview

Journal J Org Chem

Publisher American Chemical Society

Specialty Chemistry

Date 2015 Jul 14

PMID 26167866

Citations 10

Authors

Trevor A Hamlin

Christopher B Kelly

John M Ovian

Rebecca J Wiles

Leon J Tilley

Nicholas E Leadbeater

Affiliations

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Abstract

A range of oxoammonium salt-based oxidation reactions have been explored computationally using density functional theory (DFT), and the results have been correlated with experimentally derived trends in reactivity. Mechanistically, most reactions involve a formal hydride transfer from an activated C-H bond to the oxygen atom of the oxoammonium cation. Several new potential modes of reactivity have been uncovered and validated experimentally.

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