Discovery, scope, and limitations of an N-dealkylation/N-arylation of secondary sulfonamides under Chan–Lam conditions
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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.
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
Asian Journal of Organic Chemistry
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DescriptionAuthors thank the University of St Andrews for a PhD studentship (MJW) and additional funding (BT).
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