- Sequential one pot double C[sbnd]H heteroarylation of thiophene using bromopyridines to synthesize unsymmetrical 2,5-bipyridylthiophenes
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We present C[sbnd]H heteroarylation reactions between thiophene and variously substituted bromopyridines. The objective was to synthesize unsymmetrical 2,5-bipyridylthiophenes. We studied the reaction conditions allowing to a sequential one-pot double C[sbnd]H heteroarylation, in a view to introduce two different pyridyl moieties at positions 2 and 5 of the thiophene ring using bromopyridines. 11 original unsymmetrical 2,5-bipyridylthiophenes were synthesized and characterized, including 2,5-di(pyridin-2-yl)thiophenes for which the preparation by classical cross-coupling reactions is challenging. Finally, with the additional synthesis of both an unsymmetrical 2,5-biarylthiophene and an original pyrimidin-thiophene-furan scaffold, we shown that our methodology was also an efficient tool to access to new heterocyclic sequences.
- Kieffer, Charline,Babin, Victor,Jouanne, Marie,Slimani, Ikram,Berhault, Yohann,Legay, Rémi,Sopková-de Oliveira Santos, Jana,Rault, Sylvain,Voisin-Chiret, Anne Sophie
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p. 5509 - 5516
(2017/08/22)
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- Copper-catalyzed Hiyama coupling of (hetero)aryltriethoxysilanes with (hetero)aryl iodides
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A CuI-catalyzed Hiyama coupling was achieved, which proceeds in the absence of an ancillary ligand for aryl-heteroaryl and heteroaryl-heteroaryl couplings. A P,N-ligand is required to obtain the best product yields for aryl-aryl couplings. In addition to facilitating transmetalation, CsF is also found to function as a stabilizer of the [CuAr] species, potentially generated as an intermediate after transmetalation of aryltriethoxysilanes with Cu I-catalysts in the absence of ancillary ligands.
- Gurung, Santosh K.,Thapa, Surendra,Vangala, Adarsh S.,Giri, Ramesh
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supporting information
p. 5378 - 5381
(2013/11/06)
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- Radical dearomatization of arenes and heteroarenes
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The stannane-mediated benzeneselenol-catalyzed addition of aryl iodides to a range of arenes and aromatic hetereocycles has been studied. With furan, thiophene, and several carbocyclic arenes, the addition takes place with quenching of the adduct radical by the catalytic selenol leading to moderate yields of aryl-dihydroarenes. With nitrogen heterocycles, on the other hand, it was not possible to suppress aromatization of the adduct radical and fully aromatized products were isolated. Aryl iodides bearing hydrogen bond donating groups in the ortho-position add to nitrogen heterocycles with high selectivity ortho- to the nitrogen, affording a simple one-step synthesis of potential chelating ligands. While 2-iodophenol is an excellent aryl radical source in these reactions, the homologous 1-iodo-2-naphthol fails owing to its reaction with diphenyl diselenide, which gives 1-phenylseleno-2-naphthol in high yield.
- Crich, David,Patel, Mitesh
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p. 7824 - 7837
(2007/10/03)
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- Direct synthesis of heterobiaryls by radical addition to pyridine: Expeditious synthesis of chelating ligands
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The addition of aryl radicals to pyridine may be affected in moderate yield on exposure of aryl iodides to tributyltin hydride, AIBN, and diphenyl diselenide in hot pyridine. Mixtures of ortho-, meta-, and para-aryl substituted pyridines are typically obtained. When the iodide is ortho-substituted with a hydrogen bond donor, such as o-iodophenol, significantly improved selectivity for ortho-substituted pyridines, with potential as bidentate chelating ligands, is obtained.
- Crich, David,Patel, Mitesh
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p. 499 - 504
(2007/10/03)
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- ARYLATION OF HETEROCYCLES IN THE REACTION OF HETEROCYCLIC MERCURY DERIVATIVES IN THE PRESENCE OF PALLADIUM COMPLEXES
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A convenient method is proposed for the synthesis of aryl derivatives of heterocyclic compounds by the coupling reaction of heterocyclic mercury derivatives and tin derivatives with aryl and heteryl iodides in the presence of palladium complexes.In the case of organotin compounds, the reaction proceeds without the formation of side-products although mercury derivative are usually more available.
- Bumagin, N. A.,Kalinovskii, I. O.,Beletskaya, I. P.
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p. 1159 - 1162
(2007/10/02)
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