Electrically-driven N(sp2)-C(sp2/3) bond cleavage in sulfonamides
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Colleges, School and Institutes
Sulfonamides are a privileged class of functional groups in medicinal chemistry and an important class of protecting groups in organic synthesis. We report the discovery and development of unexpected electrically driven N(sp2)–C(sp2) and N(sp2)–C(sp3) bond cleavage reactions alongside a dehydrogenative C–O bond coupling reaction under batch and electroflow conditions. Intra-molecular trapping experiments with the diuretic hydrochlorothiazide gave insight into the intermediacy of an N-sulfonyliminium ion en route to the related drug metabolite, chlorothiazide. Using only electrons as the oxidant, this is a green and sustainable technological advancement for sulfonamide deprotection chemistry and drug metabolism studies.
|Journal||ACS Sustainable Chemistry & Engineering|
|Early online date||10 Feb 2020|
|Publication status||Published - 2 Mar 2020|
- Electrosynthesis, Dealkylation, Sulfonamide, Oxidation, Shono, Dehydrogenative Coupling