Accessing Alkoxy Radicals via Frustrated Radical Pairs: Diverse Oxidative Functionalizations of Tertiary Alcohols
Minsoo Ju1, Sukwoo Lee1, Halle M Marvich1
1Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, United States.
Abstract:
Alkoxy radicals are versatile reactive intermediates in organic synthesis. Here, we leverage the principle of frustrated radical pair to provide convenient access to these highly reactive species directly from tertiary alcohols via oxoammonium-mediated oxidation of the corresponding alkoxides. This approach enabled various synthetically useful transformations including β-scission, radical cyclization, and remote C-H functionalization, giving rise to versatile alkoxyamines that can be further elaborated to various functionalities.
Related Concept Videos
Radical Anti-Markovnikov Addition to Alkenes: Overview
Radical Oxidation of Allylic and Benzylic Alcohols
Oxidation of Alcohols
The process of oxidation in a chemical reaction is observed in any of the three forms:
Alkynes to Carboxylic Acids: Oxidative Cleavage
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids
Radical Reactivity: Overview


