2876-35-9Relevant academic research and scientific papers
Heterogeneous Nickel-Catalyzed Cross-Coupling between Aryl Chlorides and Alkyllithiums Using a Polystyrene-Cross-Linking Bisphosphine Ligand
Yamazaki, Yuki,Arima, Nozomi,Iwai, Tomohiro,Sawamura, Masaya
supporting information, p. 2250 - 2254 (2019/03/21)
A polystyrene-cross-linking bisphosphine ligand PS-DPPBz was used for Ni-catalyzed cross-coupling with organolithiums. A bench-stable precatalyst [NiCl2(PS-DPPBz)] enabled efficient coupling reactions between aryl chlorides and alkyllithiums. The heterogeneous Ni system showed good reusability. (Figure presented.).
Benzo polyaza and phosphole oxygen ligand and complex containing same, preparation method and application
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Paragraph 0160; 0161; 0162; 0163; 0164; 0165, (2019/01/16)
The invention discloses a benzo polyaza and phosphole oxygen ligand and a complex containing same, a preparation method and application. The invention provides a benzo polyaza and phosphole oxygen ligand as shown in formula I and a complex containing same. A complex of the benzo polyaza and phosphole oxygen ligand and a transition metal halide enables direct coupling of carbon-carbon bonds betweenbig steric hindrance alkyl and aryl; the reaction conditions are gentle; the catalyzing efficiency is high; the coupling reaction process of the carbon-carbon bonds between big steric hindrance alkyland aryl can be extremely simplified; the practicability is high; the reaction cost can be obviously decreased, and the reaction period is reduced; the complex is free from other side products without being required in the catalyzing process. The formula refers to the description.
Copolymer-incarcerated nickel nanoparticles with N-heterocyclic carbene precursors as active cross-linking agents for Corriu-Kumada-Tamao reaction
Soule, Jean-Francois,Miyamura, Hiroyuki,Kobayashi, Shu
supporting information, p. 10602 - 10605 (2013/08/23)
We have developed heterogeneous polymer-incarcerated nickel nanoparticles (NPs), which catalyze cross-coupling reactions. The matrix structure of these catalysts incorporates both N-heterocyclic carbenes (NHCs) as ligands and Ni-NPs, thanks to a new design of cross-linking agents in polymer supports. These embedded NHCs were detected by field gradient swollen-resin magic angle spinning NMR analysis. They were successfully applied to Corriu-Kumada-Tamao reactions with a broad substrate scope including functional group tolerance, and the catalyst could be recovered and reused several times without loss of activity.
Nickel-catalyzed Kumada cross-coupling reactions of tertiary alkylmagnesium halides and aryl bromides/triflates
Joshi-Pangu, Amruta,Wang, Chao-Yuan,Biscoe, Mark R.
supporting information; experimental part, p. 8478 - 8481 (2011/06/25)
We report a Ni-catalyzed process for the cross-coupling of tertiary alkyl nucleophiles and aryl bromides. This process is extremely general for a wide range of electrophiles and generally occurs with a ratio of retention to isomerization >30:1. The same procedure also accommodates the use of aryl triflates, vinyl chlorides, and vinyl bromides as the electrophilic component.
Microwave-assisted regioselective alkylation of naphthalene compounds using alcohols and zeolite catalysts
Yamashita, Hiroshi,Mitsukura, Yumi,Kobashi, Hiroko,Hiroki, Kazuaki,Sugiyama, Jun-ichi,Onishi, Kiyotaka,Sakamoto, Tetsuo
experimental part, p. 145 - 149 (2010/08/20)
Regioselective alkylation of naphthalene compounds with alcohols smoothly proceeded in the presence of zeolite catalysts under microwave irradiation. A H-mordenite (H-M) zeolite catalyst (SiO2/Al2O3 ratio = 240) showed the highest efficiency. In the microwave reactions, high reaction rates and high selectivities for 2,6-dialkylnaphthalenes were achieved. In the best case for the reaction of 2-isopropylnaphthalene with isopropyl alcohol, the conversion and the selectivity were 43.5% and 66.4%, respectively. In di-tert-butylation of naphthalene with tert-butyl alcohol, the conversion and the selectivity reached 86.5% and 70.4%, respectively. The conversions and the selectivities were generally higher than those obtained by conventional oil bath heating.
The alkylation of naphthalene over one-dimensional fourteen-membered ring zeolites. the influence of zeolite structure and alkylating agent on the selectivity for dialkylnaphthalenes
Sugi, Yoshihiro,Maekawa, Hiroyoshi,Naiki, Hiroaki,Komura, Kenichi,Kubota, Yoshihiro
experimental part, p. 1166 - 1174 (2009/05/06)
The alkylation, i.e., isopropylation, s-butylation, and t-butylation, of naphthalene (NP) was examined over one-dimensional fourteen-membered (14-MR) zeolites: CIT-5 (CF1), UTD-1 (DON), and SSZ-53 (SFH), and compared to the results over H-mordenite (MOR)
Equatorial preference in the C-H activation of cycloalkanes: GaCl 3-catalyzed aromatic alkylation reaction
Yonehara, Fumi,Kido, Yoshiyuki,Sugimoto, Hiraku,Morita, Satoshi,Yamaguchi, Masahiko
, p. 6752 - 6759 (2007/10/03)
GaCl3 catalyzes the aromatic alkylation of naphthalene or phenanthrene using cycloalkanes. The C-C bond formation predominantly takes place at the least hindered positions of the substrates, and equatorial isomers regarding the cycloalkane moiety are generally obtained. The reaction of bicyclo[4.4.0]decane and naphthalene occurs at the 2-position of naphthalene and at the 2- or 3-carbons of the cycloalkane, and the products possess a trans configuration at the junctures and an equatorial configuration at the naphthyl groups. Notably, cis-bicyclo[4.4.0]decane turns out to be much more reactive than the trans isomer, and a turnover number "TON" up to 20 based on GaCl3 is attained. 1,2-Dimethylcyclohexane reacts similarly, and the cis isomer is more reactive than the trans isomer. Monoalkylcycloalkanes react at the secondary carbons provided that the alkyl group is smaller than tert-butyl. Adamantanes react at the tertiary 1-position. The alkylation reaction is considered to involve the C-H activation of cycloalkanes with GaCl3 at the tertiary center followed by the migration of carbocations and electrophilic aromatic substitution yielding thermodynamically stable products. The stereochemistry of the reaction reveals that GaCl 3 activates the equatorial tertiary C-H bond rather than the axial tertiary C-H bond.
Study of regioselective dialkylation of napthalene in the presence of reusable zeolite catalysts
Smith, Keith,Roberts, Simon D.,El-Hiti, Gamal A.
, p. 1552 - 1559 (2007/10/03)
Highly regioselective dialkylation of naphthalene using various alkylating agents can be achieved over zeolite catalysts. For example, the tert-butylation of naphthalene (1) using tert-butanol in cyclohexane over a dealuminated H-Mordenite (HM) zeolite has been optimised to give a 60% yield of 2,6-di-tert-butylnaphthalene (3) with a 2,6/2,7 ratio of over 50. This has been achieved by varying the reaction time, temperature, solvent, pressure, amount of tert-butanol, solvent and catalyst, Si/Al ratio of the catalyst, and the mode of addition. The zeolites can be easily regenerated by heating and reused.
Selective alkylation of naphthalene with tert-butyl alcohol over large pore zeolites
Liu, Zhongmin,Moreau, Patrice,Fajula, Francois
, p. 2653 - 2654 (2007/10/03)
HY zeolites exhibit high activity and selectivity for 2,6-di-(tert-butyl)naphthalene in the liquid phase alkylation of naphthalene with tert-butyl alcohol; moreover, the desired 2,6-isomer is easily separated from the reaction mixture by crystallization.
