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Volumn , Issue 20, 2003, Pages 3948-3957

Synthesis of Differently Disubstituted 2,2′-Bipyridines by a Modified Negishi Cross-Coupling Reaction

Author keywords

2,2 Bipyridines; Biaryls; Cross coupling; Negishi reaction

Indexed keywords

2,2' BIPYRIDINE DERIVATIVE;

EID: 0242386451     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300192     Document Type: Article
Times cited : (45)

References (73)
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    • [11d] A recent special issue of the Journal of Organometallic Chemistry outlines historically and recent developments in cross-coupling chemistry: K. Tamao, T. Hiyama, E. Negishi (Eds.); J. Organomet. Chem. 2002, 653, 1-299.
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    • note
    • The best result we were able to obtain was the formation of 5-methyl-5′-[(trimethylsilyl)ethynyl]-2,2′-bipyridine (19) in 45% yield after lithiation of our model substrate 2-chloro-5-methyl-pyridine (9) with 2 equiv. of lithium and 4 equiv. of naphthalene, transmetallation with anhydrous zinc(II) chloride and subsequent palladium-catalysed cross-coupling reaction with 2-chloro-5-[(trimethylsilyl)ethynyl]-pyridine (8). However, the very long reaction time, which was found to be essential, residual unreacted lithium, which possibly interferes in the cross-coupling step, and also the excess of naphthalene caused problems during the isolation and purification of the product.
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    • 2] did not result in a significantly higher yield but actually gave 18 only in a slightly lower yield of 49%: [23a] M. Beller, H. Fischer, W. A. Herrmann, K. Öfele, C. Broßmer, Angew. Chem. 1995, 107, 1992-1993; Angew. Chem. Int. Ed. Engl. 1995, 107, 1989-1992.
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    • 2] did not result in a significantly higher yield but actually gave 18 only in a slightly lower yield of 49%: [23a] M. Beller, H. Fischer, W. A. Herrmann, K. Öfele, C. Broßmer, Angew. Chem. 1995, 107, 1992-1993; Angew. Chem. Int. Ed. Engl. 1995, 107, 1989-1992.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.