24066-86-2Relevant academic research and scientific papers
Iron-Catalyzed Highly Enantioselective Hydrogenation of Alkenes
Lu, Dongpo,Lu, Peng,Lu, Zhan,Ren, Xiang,Sun, Yufeng,Xu, Haofeng
supporting information, p. 12433 - 12438 (2021/08/23)
Here, we reported for the first time an iron-catalyzed highly enantioselective hydrogenation of minimally functionalized 1,1-disubstituted alkenes to access chiral alkanes with full conversion and excellent ee. A novel chiral 8-oxazoline iminoquinoline ligand and its iron complex have been designed and synthesized. This protocol is operationally simple by using 1 atm of hydrogen gas and shows good functional group tolerance. A primary mechanism has been proposed by the deuterium-labeling experiments.
Platinum(II) olefin hydroarylation catalysts: Tuning selectivity for the anti-Markovnikov product
Clement, Marie L.,Grice, Kyle A.,Luedtke, Avery T.,Kaminsky, Werner,Goldberg, Karen I.
supporting information, p. 17287 - 17291 (2015/02/19)
PtII complexes containing unsymmetrical (pyri-dyl)pyrrolide ligands are shown to catalyze the hydroarylation of unactivated alkenes with selectivity for the anti-Markovnikov product. Substitution on the pyrrolide portion of the ligand allows effective tuning of the selectivity to anti-Markovnikov alkylarene products, whereas substitution on the pyridyl portion can promote competitive al-kenylarene production.
Tunable phosphoramidite ligands for asymmetric hydrovinylation: Ligands par excellence for generation of all-carbon quaternary centers
Smith, Craig R.,Hwan, Jung Lim,Zhang, Aibin,RajanBabu
experimental part, p. 2089 - 2100 (2010/02/28)
α-Alkylstyrenes undergo efficient hydrovinylation (addition of ethene) in the presence of a nickel catalyst prepared from [(allyl)NiBr] 2, Na+[BAr4]- [Ar = 3,5-bis(trifluoromethyl)phenyl], and a phosphoramidite ligand giving products in excellent yields and enantioselectivities. In many cases phosphoramidites derived from achiral 2,2′-biphenol are almost as good as ligands derived from the more expensive enantiopure 1,1′-bi(2-naphthol)s. The hydrovinylation products, which carry two versatile latent functionalities, an aryl and a vinyl group, are potentially useful for the synthesis of several important natural products containing benzylic all-carbon quaternary centers. Georg Thieme Verlag Stuttgart.
Palladium-catalyzed hydrophenylation of alkynes with sodium tetraphenylborate under mild conditions
Zeng, Hanxiang,Hua, Ruimao
, p. 558 - 562 (2008/09/17)
(Chemical Equation Presented) In an aqueous solution of acetic acid, PdCl2(PPh3)2 showed high catalytic activity for the hydrophenylation of both terminal and internal alkynes with sodium tetraphenylborate (NaBPh4) under mild conditions, affording phenyl alkenes in moderate to excellent yields.
Wittig type methylenation of ketones with bis(iodozincio)methane and ionic liquid
Yoshino, Hideaki,Kobata, Masami,Yamamoto, Yuhei,Oshima, Koichiro,Matsubara, Seijiro
, p. 1224 - 1224 (2007/10/03)
Ketones were transformed into alkenes via methylenation with bis(iodozincio)methane and ionic liquid, 1-butyl-3-methyl-imidazolium hexafluorophosphate ([bmim][PF6]) in the absence of additional metal salt such as titanium chlorides.
Novel nickel-catalyzed coupling reaction of allyl ethers with chlorosilanes, alkyl tosylates, or alkyl halides promoted by vinyl-Grignard reagent leading to allylsilanes or alkenes
Terao, Jun,Watabe, Hiroyasu,Watanabe, Hiroyuki,Kambe, Nobuaki
, p. 1674 - 1678 (2007/10/03)
A new method for a carbon-silicon or carbon-carbon bond forming reaction between allyl ethers and chlorosilanes, alkyl tosylates, or alkyl halides giving rise to allylsilanes or alkenes has been developed. This reaction proceeds efficiently at ambient temperature by the combined use of nickel catalysts and a vinyl-Grignard reagent. A possible reaction pathway involving the formation of allyl-Grignard reagents via transmetallation of π-allylnickel complexes with the vinyl-Grignard reagent and subsequent trapping of the thus formed allyl-Grignard reagents with electrophiles is proposed.
Rhodium promoted isomerisation of allylic alkoxides: A new method for enolate anion formation
Gazzard, Lewis J.,Motherwell, William B.,Sandham, David A.
, p. 979 - 993 (2007/10/03)
Transition metal mediated isomerisation of allylic alkoxides is presented as a new method for enolate anion generation. The scope and limitations of enolate formation with the catalysts [Rh(dppe)(THF)2]+ClO4- and (Ph3P)3RhCl are explored and the synthetic potential of the methodology demonstrated in the stereoselective formation and reactions of certain ketone and aldehyde enolates.
Synthesis of 1,1-Disubstituted Ethenes by Means of Sequential Cross-Coupling Reactions
Fiandanese, V.,Marchese, G.,Naso, F.,Ronzini, L.
, p. 1034 - 1036 (2007/10/02)
A variety of 1-alkenes are synthesized in 63-91percent yields by means of sequential cross-coupling reactions of Grignard reagents with readily available or commercial starting materials, in the presence of transition-metal catalysts.
