Electrically Driven N(sp 2)- C(sp 2/3) Bond Cleavage of Sulfonamides

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Electrically Driven N(sp 2)- C(sp 2/3) Bond Cleavage of 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(sp 2)- C(sp 2/3) Bond Cleavage of 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(sp 2)- C(sp 2/3) Bond Cleavage of 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

UR - http://www.scopus.com/inward/record.url?scp=85080873881&partnerID=8YFLogxK

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 -