N-formyl-stabilizing quasi-catalytic species afford rapid and selective solvent-free amination of biomass-derived feedstocks

Hu Li, Haixin Guo, Yaqiong Su, Yuya Hiraga, Zhen Fang (), Emiel J. M. Hensen, Masaru Watanabe () and Richard Lee Smith ()
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Hu Li: Nanjing Agricultural University
Haixin Guo: Tohoku University
Yaqiong Su: Eindhoven University of Technology
Yuya Hiraga: Tohoku University
Zhen Fang: Nanjing Agricultural University
Emiel J. M. Hensen: Eindhoven University of Technology
Masaru Watanabe: Tohoku University
Richard Lee Smith: Tohoku University

Nature Communications, 2019, vol. 10, issue 1, 1-13

Abstract: Abstract 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 quasi-catalytic 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.

Date: 2019
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DOI: 10.1038/s41467-019-08577-4

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