Accessing Alkoxy Radicals via Frustrated Radical Pairs: Diverse Oxidative Functionalizations of Tertiary Alcohols.

J Am Chem Soc

Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, United States.

Published: July 2024

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.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC11366976PMC
http://dx.doi.org/10.1021/jacs.4c07125DOI Listing

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