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Mechanistic insight enables practical, scalable, room temperature Chan–Lam N-arylation of N-aryl sulfonamides
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dc.contributor.author | Vantourout, Julien C. | |
dc.contributor.author | Li, Ling | |
dc.contributor.author | Bendito-Moll, Enrique | |
dc.contributor.author | Chabbra, Sonia | |
dc.contributor.author | Arrington, Kenneth | |
dc.contributor.author | Bode, Bela E. | |
dc.contributor.author | Isidro-Llobet, Albert | |
dc.contributor.author | Kowalski, John A. | |
dc.contributor.author | Nilson, Mark G. | |
dc.contributor.author | Wheelhouse, Katherine M. P. | |
dc.contributor.author | Woodard, John L. | |
dc.contributor.author | Xie, Shiping | |
dc.contributor.author | Leitch, David C. | |
dc.contributor.author | Watson, Allan J. B. | |
dc.date.accessioned | 2019-09-05T23:39:46Z | |
dc.date.available | 2019-09-05T23:39:46Z | |
dc.date.issued | 2018-09-06 | |
dc.identifier | 255932045 | |
dc.identifier | 480b4685-88e9-44f8-a585-e428ef1a84f2 | |
dc.identifier | 85053679390 | |
dc.identifier | 000447224100065 | |
dc.identifier.citation | Vantourout , J C , Li , L , Bendito-Moll , E , Chabbra , S , Arrington , K , Bode , B E , Isidro-Llobet , A , Kowalski , J A , Nilson , M G , Wheelhouse , K M P , Woodard , J L , Xie , S , Leitch , D C & Watson , A J B 2018 , ' Mechanistic insight enables practical, scalable, room temperature Chan–Lam N -arylation of N -aryl sulfonamides ' , ACS Catalysis , vol. 8 , pp. 9560-9566 . https://doi.org/10.1021/acscatal.8b03238 | en |
dc.identifier.issn | 2155-5435 | |
dc.identifier.other | RIS: urn:6BD132666F218AFE5D4FFCEB3934648E | |
dc.identifier.other | ORCID: /0000-0002-3384-271X/work/48516820 | |
dc.identifier.other | ORCID: /0000-0002-1582-4286/work/56639205 | |
dc.identifier.uri | https://hdl.handle.net/10023/18431 | |
dc.description | The authors thank the EPSRC and GSK for a studentship (JCV). | en |
dc.description.abstract | Sulfonamides are profoundly important in pharmaceutical design. C–N cross-coupling of sulfonamides is an effective method for fragment coupling and structure–activity relationship (SAR) mining. However, cross-coupling of the important N-arylsulfonamide pharmacophore has been notably unsuccessful. Here, we present a solution to this problem via oxidative Cu-catalysis (Chan–Lam cross-coupling). Mechanistic insight has allowed the discovery and refinement of an effective cationic Cu catalyst to facilitate the practical and scalable Chan–Lam N-arylation of primary and secondary N-arylsulfonamides at room temperature. We also demonstrate utility in the large scale synthesis of a key intermediate to a clinical hepatitis C virus treatment. | |
dc.format.extent | 7 | |
dc.format.extent | 693512 | |
dc.language.iso | eng | |
dc.relation.ispartof | ACS Catalysis | en |
dc.subject | Boronic acid | en |
dc.subject | Boronic ester | en |
dc.subject | Catalysis | en |
dc.subject | Chan-Lam | en |
dc.subject | Copper | en |
dc.subject | Sulfonamide | en |
dc.subject | QD Chemistry | en |
dc.subject | NDAS | en |
dc.subject | SDG 3 - Good Health and Well-being | en |
dc.subject.lcc | QD | en |
dc.title | Mechanistic insight enables practical, scalable, room temperature Chan–Lam N-arylation of N-aryl sulfonamides | en |
dc.type | Journal article | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. Centre of Magnetic Resonance | en |
dc.contributor.institution | University of St Andrews. Biomedical Sciences Research Complex | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.identifier.doi | 10.1021/acscatal.8b03238 | |
dc.description.status | Peer reviewed | en |
dc.date.embargoedUntil | 2019-09-06 |
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