Journal
SYNLETT
Volume 30, Issue 4, Pages 387-392Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0037-1611341
Keywords
reductive amination; arene hydrogenation; heterogeneous catalyst; metal nanoparticle
Categories
Funding
- Japan Society for the Promotion of Science (JSPS)
- Global COE Program
- University of Tokyo
- Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan
- Japan Science and Technology Agency (JST)
- JSPS
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Reductive cross-amination between imine intermediates generated through partial hydrogenation of aniline or nitroarene derivatives and alkylamines is an ideal method for obtaining N-alkylated cyclohexylamine derivatives; however, no such transformations have hitherto been established. Here, we report a highly selective reductive cross-amination using aniline derivatives and alkylamines catalyzed by heterogeneous Rh/Pt bimetallic nanoparticles under mild conditions. The catalyst was recovered and reused for five runs, keeping high activity. In this reaction, imine intermediates generated during the course of partial hydrogenation of aniline derivatives were trapped immediately by strongly interacting primary alkylamines with the catalyst, which caused a highly selective transformation to give the desired products, while suppressing dicyclohexylamine formation.
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