Electrically-driven N(sp2)-C(sp2/3) bond cleavage in sulfonamides

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Electrically-driven N(sp2)-C(sp2/3) bond cleavage in sulfonamides. / Wetzel, Annica; Jones, Alan M.

In: ACS Sustainable Chemistry & Engineering, Vol. 8, No. 8, 02.03.2020, p. 3487–3493.

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@article{392473b0b96741b39428ddb1852b28b1,
title = "Electrically-driven N(sp2)-C(sp2/3) bond cleavage in sulfonamides",
abstract = "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.",
keywords = "Electrosynthesis, Dealkylation, Sulfonamide, Oxidation, Shono, Dehydrogenative Coupling",
author = "Annica Wetzel and Jones, {Alan M}",
year = "2020",
month = mar
day = "2",
doi = "10.1021/acssuschemeng.0c00387",
language = "English",
volume = "8",
pages = "3487–3493",
journal = "ACS Sustainable Chemistry & Engineering",
issn = "2168-0485",
publisher = "American Chemical Society",
number = "8",

}

RIS

TY - JOUR

T1 - Electrically-driven N(sp2)-C(sp2/3) bond cleavage in sulfonamides

AU - Wetzel, Annica

AU - Jones, Alan M

PY - 2020/3/2

Y1 - 2020/3/2

N2 - 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.

AB - 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.

KW - Electrosynthesis

KW - Dealkylation

KW - Sulfonamide

KW - Oxidation

KW - Shono

KW - Dehydrogenative Coupling

U2 - 10.1021/acssuschemeng.0c00387

DO - 10.1021/acssuschemeng.0c00387

M3 - Article

VL - 8

SP - 3487

EP - 3493

JO - ACS Sustainable Chemistry & Engineering

JF - ACS Sustainable Chemistry & Engineering

SN - 2168-0485

IS - 8

ER -