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. 2020:31:S122-S129.
doi: 10.1016/j.matpr.2020.06.398. Epub 2020 Jul 16.

Metal-NHC heterocycle complexes in catalysis and biological applications: Systematic review

Mohammed Jalal  1 , Belkheir Hammouti  1 , Rachid Touzani  1 , Abdelouhaed Aouniti  1 , Ismail Ozdemir  2
Affiliations

Metal-NHC heterocycle complexes in catalysis and biological applications: Systematic review

Mohammed Jalal et al. Mater Today Proc. 2020.

Abstract

N-heterocyclic carbenes are of central importance in many domains of chemistry such as organometallic, catalysis and bioinorganic. Their great importance is due to their ability to act as ligands with a large number of transition metals. These Metal-NHCs are used as catalysts in various organic transformations with good biological properties. A wide range of Metals - NHC has been found to be useful as a catalyst in various reactions using Ru, Pd, Ir, Au and Ag. This review examines the different classes of Metal - NHCs and their applications as effective catalysts in several types of organic processes, for example the formation of amide linkage, hydrogenation, isomerization, cycloisomerization, cyclopropanation, hydrosilylation, allylation and desallylation, enol-ester synthesis, heterocycle synthesis, C - C alkyne coupling.

Keywords: Applications; Biological; Catalysis; Metal; NH-Carbenes; Synthesis.

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Conflict of interest statement

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Figures

Fig. 1
Fig. 1
The main families of NHC .
Fig. 2
Fig. 2
Synthesis of a homoenolate .
Fig. 3
Fig. 3
Milstein’s catalyst for conversion of alcohols into amides .
Fig. 4
Fig. 4
General scheme for the N-alkylation reaction via a hydrogen-borrowing pathway .
Fig. 5
Fig. 5
The five NHC / Ru complexes prepared .
Fig. 6
Fig. 6
Structure of Nolan catalysts based on Iridium .
Fig. 7
Fig. 7
Structure of Nolan catalysts based on Rhodium .
Fig. 8
Fig. 8
Palladium (II)–NHC complexes used for direct C–H activation .
Fig. 9
Fig. 9
Structure of palladium –NHC complex .
Fig. 10
Fig. 10
Structure of palladium –NHC complex for Sonogashira coupling .
Fig. 11
Fig. 11
Structure of palladium –NHC phosphine complexs for Sonogashira coupling .
Fig. 12
Fig. 12
Structure of palladium –NHC phosphine complexs for Sonogashira coupling .
Fig. 13
Fig. 13
Structure of two Ru NHC complexes based on pyrazole .
Fig. 14
Fig. 14
Structure of NHC silver complexes based on pyrazole .
Fig. 15
Fig. 15
Ruthenium NHC complexes used for N-alkylation amines in mild conditions .
Fig. 16
Fig. 16
Structure of Ruthenium NHC catalyst for direct arylation .
Fig. 17
Fig. 17
Proposed structure for gold NHC silver and copper for etherification reaction .
Fig. 18
Fig. 18
Ag(I)–NHC complexes .
Fig. 19
Fig. 19
Ag(I)–NHC complexes .
Fig. 20
Fig. 20
Structure of multi-nuclear silver-NHC based on pyrazole .
Fig. 21
Fig. 21
Structure of Ag and Au-NHC complexes .
Fig. 22
Fig. 22
Structure of Ag-NHC complexes .
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References

    1. Bourissou D., Guerret O., Gabbai F.P., Bertrand G. Chem. Rev. 2000;100:39–92. - PubMed
    1. Clyne D.S., Jin J., Genest E., Gallucci J.C., Rajan Babu T.V. Org. Lett. 2000;2:1125–1128. - PubMed
    1. J.C. Garrison, R.S. Simons, J.M. Talley, & al, Organometallics, 20 (2001) 1276–1278.
    1. Batey R.A., Shen M., Lough A.J. Org. Lett. 2002;4:1411–1414. - PubMed
    1. A.M. Magill, D.S. McGuinness, K.J. Cavell, & al, Organomet. Chem. 546 (2001) 617–618.

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