61907-95-7Relevant academic research and scientific papers
Diene hydroaminomethylation via ruthenium-catalyzed C-C bond forming transfer hydrogenation: Beyond carbonylation
Oda, Susumu,Franke, Jana,Krische, Michael J.
, p. 136 - 141 (2015/12/30)
Under the conditions of ruthenium catalyzed transfer hydrogenation using 2-propanol as terminal reductant, 1,3-dienes engage in reductive C-C coupling with formaldimines obtained in situ from 1,3,5-tris(aryl)-hexahydro-1,3,5-triazines to form homoallylic amines. Deuterium labelling studies corroborate a mechanism involving reversible diene hydroruthenation to form an allylruthenium complex that engages in turn-over limiting imine addition. Protonolysis of the resulting amidoruthenium species releases product and delivers a ruthenium alkoxide, which upon β-hydride elimination closes the catalytic cycle. These transformations, which include enantioselective variants, represent the first examples of diene hydroaminomethylation.
Synthesis of 2-ethyl-2-methyl-2,3-dihydro-1H-indole, a new insecticide exhibiting juvenile hormone activity
Petrushkina,Kalinin,Ivanova,Kheinman
, p. 1953 - 1957 (2008/02/08)
Catalytic hydroamination of isoprene gave N-(1,2-dimethylprop-2-en-1-yl) aniline in a preparative yield. By heating at 260°C the product was converted into 2-ethyl-2-methyl-2,3-dihydro-1H-indole, a new ecologically safe insecticide exhibiting a juvenile h
Palladium(II)-catalyzed amination of isoprene with aniline
Petrushkina,Mysova,Orlinkov
, p. 910 - 914 (2007/10/03)
The reaction of isoprene with aniline, catalyzed by the Pd(acac) 2-(RO)3P-CF3CO2H system, 1 : 4 : 4 [R = Me, Et; acac = (CH3CO)2CH], in MeCN provides N-(3-methylbut-2-en-1-yl)aniline with a high selectivity (up to 84%) and a nearly quantitative yield (75%). At 1 : 4 : 20 and 1 : 4 : 40 molar component ratios in the catalytic system, up to 28-31% of N,N-(2,3-dimethylprop-2-en-1-yl)aniline is formed. Telomeric reaction products appear at 1 : 2 : 4 and 1 : 1 : 10 ratios.
(η3-allyl)palladium complexes bearing diphosphinidenecyclobutene ligands: Highly active catalysts for the hydroamination of 1,3-dienes
Minami,Okamoto,Ikeda,Tanaka,Ozawa,Yoshifuji
, p. 4501 - 4503 (2007/10/03)
Room-temperature hydroamination of 1,3-dienes with aniline [Eq. (1)] is efficiently catalyzed by cationic η3-allyl palladium complexes, prepared by treating [{(η3-allyl)PdCl)}2] with 1,2-diaryl-3,4-bis[(2,4,6-tri-tert-buty
REACTION BETWEEN ISOPRENE AND ANILINE ON COMPLEX PALLADIUM CATALYSTS
Petrushkina, E. A.,Zakharkin, L. I.
, p. 1392 - 1394 (2007/10/02)
Isoprene and aniline have been reacted on the catalytic Pd(acac)2-Ph3P to form a mixture of isomeric telomers: N-(dimethyloctadien-2,7-yl-1)anilines and N-(dimethyloctadien-1,7-yl-3)anilines but on the catalytic system Pd(acac)2-Ph3P-CF3COOH the main product is a mixture of N-(methylbuten-2-yl)aniline adducts.The reaction between N-methylaniline and isoprene on the latter catalyst also gives a mixture of N-methyl and N-(methylbuten-2-yl)aniline adducts.Keywords: catalytic telomerization, terpenoid anilines.
