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Discovery, scope, and limitations of an N-dealkylation/N-arylation of secondary sulfonamides under Chan–Lam conditions
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dc.contributor.author | West, Matthew | |
dc.contributor.author | Thomson, Brodie | |
dc.contributor.author | Vantourout, Julien C. | |
dc.contributor.author | Watson, Allan J. B. | |
dc.date.accessioned | 2020-11-18T00:38:35Z | |
dc.date.available | 2020-11-18T00:38:35Z | |
dc.date.issued | 2019-11-18 | |
dc.identifier.citation | West , M , Thomson , B , Vantourout , J C & Watson , A J B 2019 , ' Discovery, scope, and limitations of an N -dealkylation/ N -arylation of secondary sulfonamides under Chan–Lam conditions ' , Asian Journal of Organic Chemistry , vol. Early View . https://doi.org/10.1002/ajoc.201900617 | en |
dc.identifier.issn | 2193-5815 | |
dc.identifier.other | PURE: 262822014 | |
dc.identifier.other | PURE UUID: 66442d47-1c55-4ea2-9dc8-6040b6802a39 | |
dc.identifier.other | ORCID: /0000-0002-1582-4286/work/65014461 | |
dc.identifier.other | Scopus: 85075376889 | |
dc.identifier.other | WOS: 000496891400001 | |
dc.identifier.uri | https://hdl.handle.net/10023/21000 | |
dc.description | Authors thank the University of St Andrews for a PhD studentship (MJW) and additional funding (BT). | en |
dc.description.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. | |
dc.language.iso | eng | |
dc.relation.ispartof | Asian Journal of Organic Chemistry | en |
dc.rights | 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 | en |
dc.subject | Arylation | en |
dc.subject | Boron | en |
dc.subject | Copper | en |
dc.subject | Cross-coupling | en |
dc.subject | Oxidation | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject.lcc | QD | en |
dc.title | Discovery, scope, and limitations of an N-dealkylation/N-arylation of secondary sulfonamides under Chan–Lam conditions | en |
dc.type | Journal article | en |
dc.description.version | Postprint | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. Sir James Mackenzie Institute for Early Diagnosis | en |
dc.identifier.doi | https://doi.org/10.1002/ajoc.201900617 | |
dc.description.status | Peer reviewed | en |
dc.date.embargoedUntil | 2020-11-18 |
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