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Synfacts 2019; 15(05): 0531
DOI: 10.1055/s-0037-1612433
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Synthesis of N-Alkylcyclohexylamines on Supported Rh/Pt Nanoparticles

Contributor(s):
Yasuhiro Uozumi
,
Shuichi Hirata
Suzuki A, Miyamura H, Kobayashi S. * The University of Tokyo, Japan
Highly Selective Reductive Cross-Amination between Aniline or Nitroarene Derivatives and Alkylamines Catalyzed by Polysilane-Immobilized Rh/Pt Bimetallic Nanoparticles.

Synlett 2019;
30: 387-392
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Further Information

Publication History

Publication Date:
15 April 2019 (online)

 
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Key words

rhodium catalysis - platinum catalysis - aniline - alkylcyclohexyl-amines

Significance

Rh/Pt bimetallic nanoparticles (NPs) supported on dimethylpolysilane and alumina (Rh/Pt–DMPSi/Al2O3) promoted the synthesis of N-alkylcyclohexylamines from anilines and the corresponding N-alkylamines to give the corresponding alkylcyclohexylamines in up >99% yield. N-Methylaniline and nitrobenzene also underwent the reductive coupling with octylamine to afford N-octylcyclohexanamine in yields of 89% and 87%, respectively.


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Comment

The authors previously reported the preparation of Rh/Pt–DMPSi/Al2O3 and its application in arene hydrogenation (J. Am. Chem. Soc. 2018, 140, 11325). In the reaction of aniline with octylamine, the catalyst was used four times without significant loss of its catalytic activity (fresh: 92% yield; fourth reuse: 90%).


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