Remote Radical Desaturation of Unactivated C-H Bonds in Amides
- PMID: 34590351
- PMCID: PMC9292639
- DOI: 10.1002/chem.202103509
Remote Radical Desaturation of Unactivated C-H Bonds in Amides
Abstract
Desaturation of inert aliphatic C-H bonds in alkanes to form the corresponding alkenes is challenging. In this communication, a new and practical strategy for remote site-selective desaturation of amides via radical chemistry is reported. The readily installed N-allylsulfonylamide moiety serves as an N radical precursor. Intramolecular 1,5-hydrogen atom transfer from an inert C-H bond to the N-radical generates a translocated C-radical which is subsequently oxidized and deprotonated to give the corresponding alkene. The commercially available methanesulfonyl chloride is used as reagent and a Cu/Ag-couple as oxidant. The remote desaturation is realized on different types of unactivated sp3 -C-H bonds. The potential synthetic utility of this method is further demonstrated by the dehydrogenation of natural product derivatives and drugs.
Keywords: alkenes; desaturation; oxidation; radical; reaction mechanism.
© 2021 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
Conflict of interest statement
The authors declare no conflict of interest.
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