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.
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
Publication
Asian Journal of Organic Chemistry
Status
Peer reviewed
ISSN
2193-5815Type
Journal article
Description
Authors thank the University of St Andrews for a PhD studentship (MJW) and additional funding (BT).Collections
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