1,1′-Methylene-3,3′-bis[(N-(tert-butyl)imidazol-2-ylidene] and Its Effect in Palladium-Catalyzed C–C Coupling

Shirin Nadri; Ezzat Rafiee; Sirous Jamali; Mohammad Joshaghani

doi:10.1055/s-0034-1379954

Synlett, Table of Contents

Synlett 2015; 26(05): 619-624
DOI: 10.1055/s-0034-1379954

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1,1′-Methylene-3,3′-bis[(N-(tert-butyl)imidazol-2-ylidene] and Its Effect in Palladium-Catalyzed C–C Coupling

Shirin Nadri

^aFaculty of Chemistry, Razi University, Kermanshah 67149, Iran Email: mjoshaghani@razi.ac.ir

,

Ezzat Rafiee

^aFaculty of Chemistry, Razi University, Kermanshah 67149, Iran Email: mjoshaghani@razi.ac.ir

,

Sirous Jamali

^bChemistry Department, Sharif University Technology, P.O. Box 11155-3615, Tehran, Iran

,

Mohammad Joshaghani*

^aFaculty of Chemistry, Razi University, Kermanshah 67149, Iran Email: mjoshaghani@razi.ac.ir

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Abstract

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Abstract

A catalytic system utilizing a chelate carbene ligand containing bulk tert-butyl groups is described for palladium-catalyzed Heck and Suzuki coupling reactions. The Heck reaction focused on the coupling of different aryl bromides with mono- and 1,1-disubstituted olefins while the Suzuki reaction involved the coupling of aryl bromides and phenylboronic acid to afford the corresponding biphenyls. The catalyst system performs well with low Pd(OAc)₂ levels (0.025 mol% Pd). In all cases with monosubstituted olefins, the trans-configured products were obtained, while the results of Heck reaction of 1,1-disubstituted olefins exhibited a high selectivity favoring the terminal product.

Key words

palladium - carbene Ligand - C–C coupling - Heck reaction - Suzuki reaction

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References

References and Notes
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