21298-53-3Relevant articles and documents
Sequential one pot double C[sbnd]H heteroarylation of thiophene using bromopyridines to synthesize unsymmetrical 2,5-bipyridylthiophenes
Kieffer, Charline,Babin, Victor,Jouanne, Marie,Slimani, Ikram,Berhault, Yohann,Legay, Rémi,Sopková-de Oliveira Santos, Jana,Rault, Sylvain,Voisin-Chiret, Anne Sophie
, p. 5509 - 5516 (2017/08/22)
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.
Radical dearomatization of arenes and heteroarenes
Crich, David,Patel, Mitesh
, p. 7824 - 7837 (2007/10/03)
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.
ARYLATION OF HETEROCYCLES IN THE REACTION OF HETEROCYCLIC MERCURY DERIVATIVES IN THE PRESENCE OF PALLADIUM COMPLEXES
Bumagin, N. A.,Kalinovskii, I. O.,Beletskaya, I. P.
, p. 1159 - 1162 (2007/10/02)
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.
