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Synlett 2015; 26(05): 619-624
DOI: 10.1055/s-0034-1379954
letter
© Georg Thieme Verlag Stuttgart · New York

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

Shirin Nadri
a   Faculty of Chemistry, Razi University, Kermanshah 67149, Iran   Email: mjoshaghani@razi.ac.ir
,
Ezzat Rafiee
a   Faculty of Chemistry, Razi University, Kermanshah 67149, Iran   Email: mjoshaghani@razi.ac.ir
,
Sirous Jamali
b   Chemistry Department, Sharif University Technology, P.O. Box 11155-3615, Tehran, Iran
,
Mohammad Joshaghani*
a   Faculty of Chemistry, Razi University, Kermanshah 67149, Iran   Email: mjoshaghani@razi.ac.ir
› Author Affiliations
Further Information

Publication History

Received: 10 October 2014

Accepted after revision: 27 November 2014

Publication Date:
14 January 2015 (online)

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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

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1379954.
  • Supporting Information
 

  • References and Notes

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