Petretto, Giacomo Luigi and Zucca, Antonio and Stoccoro, Sergio and Cinellu, Maria Agostina and Minghetti, Giovanni (2010) Step by step palladium mediated syntheses of new 2-(pyridin-2-yl)-6-R-nicotinic acids and esters. Journal of Organometallic Chemistry, Vol. 695 (2), p. 256-259. ISSN 0022-328X. Article.
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Taking advantage of palladium peculiar “rollover” C,N cyclometallation, it is possible to promote C(3) functionalization of 6-alkyl-substituted-2,2′-bipyridines. The carbonylation reaction of rollover species [Pd(Ln)Cl]2, (HL1 = 6-isopropyl-2,2′-bipy, 1; HL2 = 6-neopentyl-2,2′-bipy, 2; HL3 = 6-ethyl-2,2′-bipy, 3; HL4 = 6-methyl-2,2′-bipy, 4) allowed the synthesis of 2-(pyridin-2-yl)-6-alkyl-nicotinic acids or esters. These nicotinic derivatives are extremely rare and, as far as we know, quite unreported in the case of the 6-substituted molecules.
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