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Issue 1, 2017
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Synthesis of formamides containing unsaturated groups by N-formylation of amines using CO2 with H2

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Abstract

Formamides have wide applications in the industry and have been synthesized using CO2 as a carbon source and H2 as a reducing agent. However, previous systems required a noble catalyst and high temperature to achieve high efficiency, and the substrate scope was mostly limited to saturated amines. The selective N-formylation of amines containing unsaturated groups using CO2 and H2 is challenging because the efficient catalysts for the N-formylation are usually very active for hydrogenation of the unsaturated groups. Herein, we achieved for the first time a selective and efficient N-formylation of amines containing unsaturated groups using CO2 and H2 with a Cu(OAc)2–4-dimethylaminopyridine (DMAP) catalytic system. The substrates were converted to the desired formamides, while the unsaturated groups, such as the carbonyl group, the C[double bond, length as m-dash]C bond, C[triple bond, length as m-dash]N bond and the ester group remained. The main reason for the excellent selectivity of the Cu(OAc)2–DMAP catalytic system was that it was very active for the N-formylation reaction, but was not active for the hydrogenation of the unsaturated groups.

Graphical abstract: Synthesis of formamides containing unsaturated groups by N-formylation of amines using CO2 with H2

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Supplementary files

Article information


Submitted
12 Aug 2016
Accepted
30 Nov 2016
First published
30 Nov 2016

Green Chem., 2017,19, 196-201
Article type
Paper

Synthesis of formamides containing unsaturated groups by N-formylation of amines using CO2 with H2

H. Liu, Q. Mei, Q. Xu, J. Song, H. Liu and B. Han, Green Chem., 2017, 19, 196
DOI: 10.1039/C6GC02243J

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