- Efficient syntheses of new heteroarotinoids through functional pyridylzinc reagents and palladium-catalyzed cross-coupling reactions
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A convergent synthesis of heteroarotinoids 4, 5a, and 5b, bearing chromene rings in association with pyridyl or ethynylpyridyl moieties, from 6-bromo-2-pyridylzinc chloride (11) is described. This new functional heteroarylzinc reagent, readily accessible
- Alami, Mouad,Peyrat, Jean-Francois,Belachmi, Larbi,Brion, Jean-Daniel
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- Selective palladium-catalysed arylation of 2,6-dibromopyridine using N-heterocyclic carbene ligands
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A selective palladium-catalysed arylation of 2,6-dibromopyridine has been developed by employing N-heterocyclic carbene ligands. Selective mono-arylation was performed in water/acetonitrile solvent system at ambient temperature with catalyst loading of 0.1 mol%. This reaction was also found to proceed smoothly in water although at a slightly elevated temperature of 80 °C. 2,6-Disubstituted and diversely substituted 2,6-pyridines were also obtained in high yields which will be of importance to organic and medicinal chemists.
- Prajapati,Schulzke,Kindermann,Kapdi
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p. 53073 - 53085
(2015/06/25)
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- Palladium-catalyzed synthesis of nonsymmetrically functionalized bipyridines, poly(bipyridines) and terpyridines
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Palladium-catalyzed coupling reactions were employed to prepare nonsymmetric, densely functionalized bipyridines and oligo(bipyridines), featuring sensitive functionalities like alcohol, ester and aldehyde groups. Stille coupling between halo (poly)pyridine and the proper (poly)pyridyltin derivative afforded in good yields nonsymmetric, derivatized oligo(bipyridines), amenable to further synthetic modifications. The methodology was used also to synthesize highly functionalized terpyridines. A series of Suzuki and Stille palladium-promoted coupling reactions allowed us to obtain in good yields terpyridines bearing two different and differently functionalizable groups, valuable building blocks for the construction of complex supramolecular frameworks. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
- Puglisi, Alessandra,Benaglia, Maurizio,Roncan, Giulia
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p. 1552 - 1558
(2007/10/03)
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- Syntheses of substituted pyridines, quinolines and diazines via palladium-catalyzed cross-coupling of aryl Grignard reagents
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The palladium-catalyzed cross-coupling reactions between arylmagnesium halides (phenylmagnesium chloride, mesitylmagnesium bromide, 4-(methoxycarbonyl)phenylmagnesium chloride and 4-cyanophenylmagnesium chloride) and halopyridines allowed the synthesis of substituted pyridines. Owing to the remarkably mild conditions used (often below 0°C), the reaction could be extended to the use of functionalized halopyridines, haloquinolines and halodiazines.
- Bonnet, Véronique,Mongin, Florence,Trécourt, Fran?ois,Quéguiner, Guy,Knochel, Paul
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p. 4429 - 4438
(2007/10/03)
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