Copper‐Catalyzed Amination of Congested and Functionalized α‐Bromocarboxamides with either Amines or Ammonia at Room Temperature

There are several reports on the synthesis of alkylamines, but most of the reported methods are not suitable for the synthesis of hindered amines. In this research, we found that a copper catalyst is effective for the formation of congested C−N bonds at room temperature. Control experiments revealed...

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Bibliographic Details
Published in:Angewandte Chemie 2017-09, Vol.129 (38), p.11768-11772
Main Authors: Ishida, Syo, Takeuchi, Kentaro, Taniyama, Nobuhiro, Sunada, Yusuke, Nishikata, Takashi
Format: Article
Language:English
Subjects:
Alkylierungen
Amide
Aminierungen
Kupfer
Reaktionsmechanismen
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Summary:There are several reports on the synthesis of alkylamines, but most of the reported methods are not suitable for the synthesis of hindered amines. In this research, we found that a copper catalyst is effective for the formation of congested C−N bonds at room temperature. Control experiments revealed that a copper amide is a key intermediate. Moreover, when a chiral amine was used, a quaternary carbon stereogenic center was created with good selectivity. Platzfrage: Unter Kupferkatalyse reagieren sperrige und funktionalisierte Alkylsubstrate bei Raumtemperatur mit Aminen oder Ammoniak. Das Schlüsselintermediat dieser Aminierungen ist ein Kupferamid.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201706293