Nickel(0)‐Catalyzed Hydroalkenylation of Imines with Styrene and Its Derivatives

A nickel(0)‐catalyzed hydroalkenylation of imines with styrene and its derivatives is described. A wide range of aromatic and aliphatic imines directly coupled with styrene and its derivatives, thus providing various synthetically useful allylic amines with up to 95 % yield. The reaction offers a ne...

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Published inAngewandte Chemie Vol. 130; no. 13; pp. 3454 - 3458
Main Authors Xiao, Li‐Jun, Zhao, Chao‐Yue, Cheng, Lei, Feng, Bo‐Ya, Feng, Wei‐Min, Xie, Jian‐Hua, Xu, Xiu‐Fang, Zhou, Qi‐Lin
Format Journal Article
LanguageEnglish
German
Published Weinheim Wiley Subscription Services, Inc 19.03.2018
Subjects
Aliphatic compounds
Alkene
Alkenes
Allylverbindungen
Amines
Chemistry
Derivatives
Imine
Imines
Mathematical analysis
Nickel
Reagents
Reaktionsmechanismen
Styrene
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Summary:A nickel(0)‐catalyzed hydroalkenylation of imines with styrene and its derivatives is described. A wide range of aromatic and aliphatic imines directly coupled with styrene and its derivatives, thus providing various synthetically useful allylic amines with up to 95 % yield. The reaction offers a new atom‐ and step‐economical approach to allylic amines by using alkenes instead of alkenyl‐metallic reagents. Experiments and DFT calculations showed that TsNH2 promotes the proton transfer from the coordinated olefin to the imine, accompanied by a new C−C bond formation. Ohne Metallreagentien: Die Nickel(0)‐katalysierte Hydroalkenylierung von Iminen mit Styrol und Styrolderivaten bietet einen neuen atomökonomischen und direkten Ansatz für die Synthese von Allylaminen ausgehend von Alkenen anstelle von Alkenylmetallreagentien. PG=Schutzgruppe, Ts=4‐Toluolsulfonyl.
Bibliography:ObjectType-Article-1
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ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201713333