N-heterocyclic NCN-pincer palladium complexes: A source for general, highly efficient catalysts in Heck, Suzuki, and Sonogashira coupling reactions

Synlett

Volumn , Issue 20, 2005, Pages 3116-3120

  Churruca, Fátima ^a   SanMartin, Raul ^a   Tellitu, Imanol ^a   Domínguez, Esther ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

Catalysis; Cross coupling; Palladacycles; Pincer complexes

Indexed keywords

BROMIDE; HETEROCYCLIC COMPOUND; IODIDE; LIGAND; METAL COMPLEX; PALLADIUM COMPLEX;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CROSS COUPLING REACTION; HECK REACTION; SONOGASHIRA REACTION; SUZUKI REACTION;

EID: 29744470431     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-922754     Document Type: Article

References (48)

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39. Similar reaction conditions employing a silica-supported tetradentate NHC catalyst were performed by: Zhao, Y.; Zhou, Y.; Ma, D.; Liu, J.; Li, L.; Zhang, T. Y.; Zhang, H. Org. Biomol. Chem. 2003, 1, 1643.
40. 1H NMR spectroscopy [using bis(ethylene glycol) dimethyl ether as an internal standard]; the identity of every product was confirmed by comparison with spectroscopic data in the literature.
41. NCN-, PCP-, CNC-, and NCP-pincer complexes have been used as catalysts in Suzuki coupling reactions, TON values varying from 20 to 177500, see: (a) Bedford, R. B.; Draper, S. M.; Scully, P. N.; Welch, S. L. New J. Chem. 2000, 24, 745.
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45. 1H NMR spectroscopy [using bis(ethylene glycol) dimethyl ether as an internal standard]; the identity of every product was confirmed by comparison with spectroscopic data in the literature.
46. The highest value (80,000) was achieved by reaction of 4-chlorobenzene and 1-octyne in the presence of catalyst 2b (Table 3, entry 14). When 0.01 mol% Pd was employed, 100% conversion and 80% yield for the corresponding 1-phenyloctyne were obtained; TOF = 4444.
47. To the best of our knowledge, three examples of Sonogashira coupling reactions catalyzed by palladium pincer complexes have been reported so far, exhibiting TON values of 20-100, see: (a) Eberhard, M. R.; Wang, Z.; Jensen, C. M. Chem. Commun. 2002, 818.
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