2019年2月
N-formyl-stabilizing quasi-catalytic species afford rapid and selective solvent-free amination of biomass-derived feedstocks
NATURE COMMUNICATIONS
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- 巻
- 10
- 号
- 1
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1038/s41467-019-08577-4
- 出版者・発行元
- NATURE PUBLISHING GROUP
Nitrogen-containing compounds, especially primary amines, are vital building blocks in nature and industry. Herein, a protocol is developed that shows in situ formed N-formyl quasicatalytic species afford highly selective synthesis of formamides or amines with controllable levels from a variety of aldehyde-and ketone-derived platform chemical substrates under solvent-free conditions. Up to 99% yields of mono-substituted formamides are obtained in 3 min. The C-N bond formation and N-formyl species are prevalent in the cascade reaction sequence. Kinetic and isotope labeling experiments explicitly demonstrate that the C-N bond is activated for subsequent hydrogenation, in which formic acid acts as acid catalyst, hydrogen donor and as N-formyl species source that stabilize amine intermediates elucidated with density functional theory. The protocol provides access to imides from aldehydes, ketones, carboxylic acids, and mixed-substrates, requires no special catalysts, solvents or techniques and provides new avenues for amination chemistry.
- リンク情報
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- DOI
- https://doi.org/10.1038/s41467-019-08577-4
- Web of Science
- https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000458297200003&DestApp=WOS_CPL
- Scopus Url
- http://www.scopus.com/inward/record.url?eid=2-s2.0-85061290909&partnerID=MN8TOARS
- ID情報
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- DOI : 10.1038/s41467-019-08577-4
- ISSN : 2041-1723
- ORCIDのPut Code : 75016159
- SCOPUS ID : 85061290909
- Web of Science ID : WOS:000458297200003