Discovery, scope, and limitations of an N-dealkylation/N-arylation of secondary sulfonamides under Chan–Lam conditions

Matthew West; Brodie Thomson; Julien C. Vantourout; Allan J. B. Watson

doi:10.1002/ajoc.201900617

Discovery, scope, and limitations of an N-dealkylation/N-arylation of secondary sulfonamides under Chan–Lam conditions

Matthew West, Brodie Thomson, Julien C. Vantourout, Allan J. B. Watson

School of Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

We report the discovery, scope, and limitations of a Cu‐mediated sulfonamide N‐dealkylation/N‐arylation reaction. Specific secondary N‐alkyl sulfonamides undergo Cu‐mediated oxidative dealkylation followed by N‐arylation under Chan–Lam conditions. The reaction is relatively general, allowing the synthesis of a range of N‐aryl secondary sulfonamides in good yield. Mechanistic investigations determined the sequence of reaction events as well as the efficiency‐limiting events. Limitations in the methodology are also presented.

Original language	English
Journal	Asian Journal of Organic Chemistry
Volume	Early View
Early online date	18 Nov 2019
DOIs	https://doi.org/10.1002/ajoc.201900617
Publication status	E-pub ahead of print - 18 Nov 2019

Keywords

Arylation
Boron
Copper
Cross-coupling
Oxidation

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10.1002/ajoc.201900617

Accepted Article
Copyright © 2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim. This work has been made available online in accordance with publisher policies or with permission. Permission for further reuse of this content should be sought from the publisher or the rights holder. This is the author created accepted manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1002/ajoc.201900617
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Cite this

@article{66442d471c554ea29dc86040b6802a39,

title = "Discovery, scope, and limitations of an N-dealkylation/N-arylation of secondary sulfonamides under Chan–Lam conditions",

abstract = "We report the discovery, scope, and limitations of a Cu‐mediated sulfonamide N‐dealkylation/N‐arylation reaction. Specific secondary N‐alkyl sulfonamides undergo Cu‐mediated oxidative dealkylation followed by N‐arylation under Chan–Lam conditions. The reaction is relatively general, allowing the synthesis of a range of N‐aryl secondary sulfonamides in good yield. Mechanistic investigations determined the sequence of reaction events as well as the efficiency‐limiting events. Limitations in the methodology are also presented.",

keywords = "Arylation, Boron, Copper, Cross-coupling, Oxidation",

author = "Matthew West and Brodie Thomson and Vantourout, \{Julien C.\} and Watson, \{Allan J. B.\}",

note = "Authors thank the University of St Andrews for a PhD studentship (MJW) and additional funding (BT).",

year = "2019",

month = nov,

day = "18",

doi = "10.1002/ajoc.201900617",

language = "English",

volume = "Early View",

journal = "Asian Journal of Organic Chemistry",

issn = "2193-5815",

publisher = "Wiley-VCH, Weinheim",

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T1 - Discovery, scope, and limitations of an N-dealkylation/N-arylation of secondary sulfonamides under Chan–Lam conditions

AU - West, Matthew

AU - Thomson, Brodie

AU - Vantourout, Julien C.

AU - Watson, Allan J. B.

N1 - Authors thank the University of St Andrews for a PhD studentship (MJW) and additional funding (BT).

PY - 2019/11/18

Y1 - 2019/11/18

N2 - We report the discovery, scope, and limitations of a Cu‐mediated sulfonamide N‐dealkylation/N‐arylation reaction. Specific secondary N‐alkyl sulfonamides undergo Cu‐mediated oxidative dealkylation followed by N‐arylation under Chan–Lam conditions. The reaction is relatively general, allowing the synthesis of a range of N‐aryl secondary sulfonamides in good yield. Mechanistic investigations determined the sequence of reaction events as well as the efficiency‐limiting events. Limitations in the methodology are also presented.

AB - We report the discovery, scope, and limitations of a Cu‐mediated sulfonamide N‐dealkylation/N‐arylation reaction. Specific secondary N‐alkyl sulfonamides undergo Cu‐mediated oxidative dealkylation followed by N‐arylation under Chan–Lam conditions. The reaction is relatively general, allowing the synthesis of a range of N‐aryl secondary sulfonamides in good yield. Mechanistic investigations determined the sequence of reaction events as well as the efficiency‐limiting events. Limitations in the methodology are also presented.

KW - Arylation

KW - Boron

KW - Copper

KW - Cross-coupling

KW - Oxidation

UR - https://www.scopus.com/pages/publications/85075376889

U2 - 10.1002/ajoc.201900617

DO - 10.1002/ajoc.201900617

M3 - Article

SN - 2193-5815

VL - Early View

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

ER -

Discovery, scope, and limitations of an N-dealkylation/N-arylation of secondary sulfonamides under Chan–Lam conditions

Abstract

Keywords

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Data underpinning "Discovery, scope, and limitations of an N-dealkylation/N-arylation of secondary sulfonamides under Chan–Lam conditions"

Methods for C-C and C-N bond formation using earth-abundant metals

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Discovery, scope, and limitations of an N-dealkylation/N-arylation of secondary sulfonamides under Chan–Lam conditions

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Datasets

Data underpinning "Discovery, scope, and limitations of an N-dealkylation/N-arylation of secondary sulfonamides under Chan–Lam conditions"

Student theses

Methods for C-C and C-N bond formation using earth-abundant metals

Cite this