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Indirect synthesis of methyl and alkylamines from CO2

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HAL Id: cea-02346341

https://hal-cea.archives-ouvertes.fr/cea-02346341

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Indirect synthesis of methyl and alkylamines from CO2

S Savourey, T Nasr-Allah, G Lefèvre, J.C. Berthet, Thibault Cantat

To cite this version:

S Savourey, T Nasr-Allah, G Lefèvre, J.C. Berthet, Thibault Cantat. Indirect synthesis of methyl and alkylamines from CO2. 4th CARlsMA Meeting - Catalityc Routines for Small Molecule Activation, Mar 2016, Ljubljana, Slovenia. �cea-02346341�

(2)

4th CARlsMA Meeting - Catalityc Routines for Sm ail Molecule Activation

Indirect synthesis of methyl and alkylamines from CO

2

S. Savourey,1 T. Nasr-Allah, 1 G. Lefèvre, 1

J.c.

Berthet, 1 T. Cantat *1

LCMCE, CEA Saclay, 91191 Gif-sur-Yvette cedex.

e-mail: solene.savourey@hotmailfr

In the past few years C02 has been investigated as a Cl building block for the synthesis of a variety of chemicals and especially methylamines.1 However due to the inertness of CO2, the methylation of amines re~.Juire either the use of activated hydrides (silanes/boranes) whose by-products are not recyc1able, or the use oflarge excess ofH2 yie1ding poor faradaic efficiencies. On the other hand, great improvements have been made for the 2-e1ectron reduction of CO2 to CO or HCOO- offering convenient platforms for the indirect synthesis of chemicals form C02.2 However to the best of our knowledge, neither HCOO- nor CO has been reported for the synthesis of methyl or alkylamines.

We therefore report the first ruthenium catalyzed synthesis of methylamines using HCOOH as the unique source of carbon and hydrogen.3 Thanks to a theoretical and experimental approach,4 we were able to achieve quantitative yield for the methylation of amines. If the use of HCOOH is lin;üted to the synthesis of methylamines, we also deve10ped the synthesis of alkylamines via the homologation of amines, using CO as a building block.5 Amines bearing an alkyl chain of up to 5 carbons were synthetized from the corresponding methylamines in one pot thanks to a cobalt catalyst.

R2 [Ru]! R2 R{NH ( R{N'CH 3

C02

~

HCOOH CO R2 L ~2 H2 H2 R{N, [Co] { red. R{N,C'C,C-C, H2 H2 References

1. A. Tlili, E. Blondiaux, X. Frogneux, T. Cantat, Green. Chem, 2014, 10.1039/C4GC01614A.

2. J. Qiao, Y. Liu, F. Hong, J. Zhang, Chem. Soc. Rev, 2014,43,631

3. S. Savourey, G. Lefèvre, J.-C. Berthet, T. Cantat, Chem. Commun., 2014, 50,14033.

4. S. Savourey, G. Lefèvre, J.-c. Berthet, P. Thuéry, C. Genre, T. Cantat, Angew. Chem., In!. Ed.,

2014, 53, 1046

5. Manuscript on preparation

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