Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
- PMID: 28784970
- PMCID: PMC5613783
- DOI: 10.3791/54932
Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
Abstract
Detailed and generalized protocols are presented for the synthesis and subsequent purification of four palladium N-heterocyclic carbene complexes from benzimidazolium salts. Detailed and generalized protocols are also presented for testing the catalytic activity of such complexes in arylation and Suzuki-Miyaura cross-coupling reactions. Representative results are shown for the catalytic activity of the four complexes in arylation and Suzuki-Miyaura type reactions. For each of the reactions investigated, at least one of the four complexes successfully catalyzed the reaction, qualifying them as promising candidates for catalysis of many carbon-carbon bond-forming reactions. The protocols presented are general enough to be adapted for the synthesis, purification and catalytic activity testing of new palladium N-heterocyclic carbene complexes.
References
-
- Akkoc S, Gok Y. Synthesis and characterization of 1-phenyl-3-alkylbenzimidazol-2-ylidene salts and their catalytic activities in the Heck and Suzuki cross-coupling reactions. J. Coord. Chem. 2013;66(8):1396–1404.
-
- Aktas A, Akkoc S, Gok Y. Palladium catalyzed Mizoroki-Heck and Suzuki-Miyaura reactions using naphthalenomethyl-substituted imidazolidin-2-ylidene ligands in aqueous media. J. Coord. Chem. 2013;66(16):2901–2909.
-
- Cetinkaya B, Alici B, Ozdemir I, Bruneau C, Dixneuf PH. 2-imidazoline and 1,4,5,6-tetrahydropyrimidine-ruthenium(II) complexes and catalytic synthesis of furan. J. Organomet. Chem. 1999;575(2):187–192.
-
- Chouthaiwale PV, Rawat V, Sudalai A. Pd-catalyzed selective hydrosilylation of aryl ketones and aldehydes. Tetrahedron Lett. 2012;53(2):148–150.
-
- Herrmann WA. N-heterocyclic carbenes: A new concept in organometallic catalysis. Angew. Chem. Int. Ed. 2002;41(8):1290–1309. - PubMed
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Other Literature Sources