Interaction of vinylpyridines with 1,3-dienes catalyzed by transition metal complexes

Selimov, F. A.; Ptashko, O. A.; Фатыхов, А. А.; Khalikova, N. R.; Джемилев, У. М.

doi:10.1007/bf00698950

Cited by 3 publications

(2 citation statements)

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“…We have identified only one such example involving vinylpyridines – a Ni(0) catalyzed cycloaddition that, for the cycloaddition between 1 and 2, leads to a nonselective, statistical mixture of regioisomers in 30% yield. 13 Both this process and a non-selective Cp 2 ZrCl 2 -promoted reaction reported alongside the Ni(0) work require nearly the same temperature as the thermal reaction (140–150 °C).…”

Section: Resultsmentioning

confidence: 97%

Vinylazaarenes as dienophiles in Lewis acid-promoted Diels–Alder reactions

2021

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Section: Resultsmentioning

confidence: 97%

Vinylazaarenes as dienophiles in Lewis acid-promoted Diels–Alder reactions

2021

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“…115 The authors 115 propose the most probable mechanism for the interaction of 1,3-dienes with 2- A cyclocodimerization of 2-vinylpyridine with cyclopentadiene was shown to be able to give selectively norbornenylpyridines in the presence of metal complex catalysts. 117 From a number of catalysts tested on the basis of compounds Ni, Pd, Fe, Co, Cu, Rh, and Zr modified by phosphine ligands, reduced by organoaluminium and -magnesium reagents the three-component system of Ni(acac) 2 -PPh 3 -AlEt 3 (1:3:4) or a catalyst Cp 2 ZrCl 2 were found to have the highest activity on a reaction in benzene or toluene at 100-110 °C for 4-6 hours.…”

Section: Synthesis Of Cycloalkenyl-and Alkatrienylpyridines By Codimementioning

confidence: 99%

Metal complex catalysis in a synthesis of pyridine bases

Джемилев¹,

Selimov²,

Толстиков³

2002

Arkivoc

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The review systematizes for the first time literature data of the last 15 years on a synthesis of pyridine bases including those of natural structure with the use of metal complex catalysts. The catalyzed by complexes of transition metals (Co, Ni, Pd, Zr) and rare-earth elements reactions of heterocyclization of acetylenes with nitriles, liquid phase condensation of aldehydes with amines, linear and cyclic oligomerization of vinylpyridines with 1,3-dienes and condensation of carbonic acid chloroanhydrides with olefins, acetylenes, tertiary alcohols to give substituted pyridines, quinolines and phenanthrolines of a set structure are considered. The mechanisms of molecule generation of pyridine bases in the presence of metal complex catalysts are discussed, and data on an effect of transition metal nature, initial monomer structure and reaction conditions on a reaction direction of a formation of six-membered nitrogen heterocycles are listed.

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Branch-Selective Reductive Coupling of 2-Vinyl Pyridines and Imines via Rhodium Catalyzed C−C Bond Forming Hydrogenation

2008

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Hydrogenation of 2-vinyl azines 1a-1e in the presence of N-arylsulfonyl imines 2a-2l at ambient temperature and pressure employing cationic rhodium catalysts ligated by tri-2-furylphosphine results in regioselective reductive coupling to furnish branched products of imine addition 3a-3v, which embody modest to high levels of syn-diastereoselectivity. Catalytic coupling of 6-bromo-2-vinylpyridine 1a to imine 2l under an atmosphere of elemental deuterium provides deuterio-3l, with deuterium exclusively at the former beta-position of the vinyl moiety. These data are consistent with a catalytic mechanism involving oxidative coupling of the vinyl azine and imine partners to furnish a cationic aza-rhodacyclopentane, which upon deuteriolytic cleavage releases the adduct and regenerates cationic rhodium(I) to close the catalytic cycle. These studies represent the first metal catalyzed reductive C-C couplings of vinyl azines.

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Interaction of vinylpyridines with 1,3-dienes catalyzed by transition metal complexes

Cited by 3 publications

References 0 publications

Vinylazaarenes as dienophiles in Lewis acid-promoted Diels–Alder reactions

Vinylazaarenes as dienophiles in Lewis acid-promoted Diels–Alder reactions

Metal complex catalysis in a synthesis of pyridine bases

Branch-Selective Reductive Coupling of 2-Vinyl Pyridines and Imines via Rhodium Catalyzed C−C Bond Forming Hydrogenation

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