Nickel(0)-Catalyzed N-Allylation of Amides and p-Toluenesulfonamide with Allylic Alcohols under Neat and Neutral Conditions

Nickel(0)‐catalyzed direct N‐allylation of amides and p‐toluenesulfonamide with allylic alcohols took place in the presence of Ni0–diphosphine complexes. The corresponding N‐allylated (and/or N,N‐diallylated) products were obtained in moderate to high yields under neutral conditions. Amides and p‐to...

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Veröffentlicht in:European journal of organic chemistry 2016-08, Vol.2016 (22), p.3796-3803
Hauptverfasser: Azizi, Mohamed Salah, Edder, Youssef, Karim, Abdallah, Sauthier, Mathieu
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Sprache:eng
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Zusammenfassung:Nickel(0)‐catalyzed direct N‐allylation of amides and p‐toluenesulfonamide with allylic alcohols took place in the presence of Ni0–diphosphine complexes. The corresponding N‐allylated (and/or N,N‐diallylated) products were obtained in moderate to high yields under neutral conditions. Amides and p‐toluenesulfonamide are N‐allylated using allyl alcohol in a catalytic fashion. The reaction is promoted by nickel‐based catalysts and yields water as a byproduct. Interestingly, self‐etherification of allylic alcohol is a competing side reaction that yields diallyl ether.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201600500