35511-91-2Relevant academic research and scientific papers
Ni/Co-catalyzed homo-coupling of alkyl tosylates
Komeyama, Kimihiro,Tsunemitsu, Ryusuke,Michiyuki, Takuya,Yoshida, Hiroto,Osaka, Itaru
, (2019/05/02)
A direct reductive homo-coupling of alkyl tosylates has been developed by employing a combination of nickel and nucleophilic cobalt catalysts. A single-electron-transfer-type oxidative addition is a pivotal process in the well-established nickel-catalyzed coupling of alkyl halides. However, the method cannot be applied to the homo-coupling of ubiquitous alkyl tosylates due to the high-lying σ*(C–O) orbital of the tosylates. This paper describes a Ni/Co-catalyzed protocol for the activation of alkyl tosylates on the construction of alkyl dimers under mild conditions.
High conversion of styrene, ethylene, and hydrogen to linear monoalkylbenzenes
Lamparelli, David Hermann,Ricca, Antonio,Palma, Vincenzo,Oliva, Leone
, (2018/06/06)
1-Alkylbenzenes as a precursor of surfactants, can be produced from ethylene, styrene, and hydrogen. These intermediates, lacking tertiary carbons, are environmentally more benign than commercial ones that bear the aromatic ring linked to an internal carbon of the aliphatic chain. The one-pot synthesis of highly linear 1-alkylbenzenes (LABs) through the homogeneous catalysis of olefin poly-insertion from cheap and largely available reagents can be carried out with a high turnover and selectivity. A purposely designed reactor that allows for the fine control of the three components feed, along with temperature, plays a key role in this achievement. A turnover of 194 g of LABs per mmol of catalyst per hour can be obtained with the simultaneous removal of polyethylene as a by-product.
Remote migratory cross-electrophile coupling and olefin hydroarylation reactions enabled by in situ generation of nih
Chen, Fenglin,Chen, Ke,Zhang, Yao,He, Yuli,Wang, Yi-Ming,Zhu, Shaolin
supporting information, p. 13929 - 13935 (2017/11/07)
A highly efficient strategy for remote reductive cross-electrophile coupling has been developed through the ligand-controlled nickel migration/arylation. This general protocol allows the use of abundant and bench-stable alkyl bromides and aryl bromides for the synthesis of a wide range of structurally diverse 1, 1-diarylalkanes in excellent yields and high regioselectivities under mild conditions. We also demonstrated that alkyl bromide could be replaced by the proposed olefin intermediate while using n-propyl bromide/Mn0 as a potential hydride source.
Metathesis of renewable polyene feedstocks – Indirect evidences of the formation of catalytically active ruthenium allylidene species
Kovács, Ervin,Sághy, Péter,Turczel, Gábor,Tóth, Imre,Lendvay, Gy?rgy,Domján, Attila,Anastas, Paul T.,Tuba, Róbert
supporting information, p. 213 - 217 (2017/09/12)
Cross-metathesis (CM) of conjugated polyenes, such as 1,6-diphenyl-1,3,5-hexatriene (1) and α-eleostearic acid methyl ester (2) with several olefins, including 1-hexene, dimethyl maleate and cis-stilbene as model compounds has been carried out using (1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene)-dichloro(o-isopropoxyphenylmethylene)ruthenium (Hoveyda-Grubbs 2nd generation, HG2) catalyst. The feasibility of these reactions is demonstrated by the observed high conversions and reasonable yields. Thus, regardless of the relatively low electron density, =CH–CH= conjugated units of molecules, including compound 2 as a sustainable, non-foodstuff source, can be utilized as building blocks for the synthesis of various value-added chemicals via olefin metathesis. DFT-studies and the product spectrum of the self-metathesis of 1,6-diphenyl-1,3,5-hexatriene suggest that a Ru η1-allylidene complex is the active species in the reaction.
Electrosynthesis of Organic Compounds, VII. Electrochemical Oxidation of Selected Arylalkyl Halides
Ismail, M. T.,Abdel-Wahab, A. A.,El-Khawaga, A. M.,Mohamed, O. S.,Khalaf, A. A.
, p. 23 - 25 (2007/10/02)
Anodic oxidation of selected arylalkyl halides was carried out in methanol containing 0.05 mol.l-1 Ba(ClO4)2, as electrolyte on a platinum anode at + 1.7 V vs SCE.The compounds electrochemically oxidized were benzyl bromide (1), 2-phenylethyl bromide (2), 3-phenylpropyl bromide (3), 4-phenylbutyl chloride (4), 1-methyl-3-phenylpropyl chloride (5) and 1,1-dimethyl-3-phenylpropyl chloride (6).The principal products isolated were the corresponding alkylbenzenes, alkenylbenzenes, dimers, ethers and cyclic products.Mechanisms were suggested.Also, kinetic studies were carried out on carbon-halogen bond cleavage of the compounds investigated (1-6).Current-potential curves were drawn, and discharge oxidation potentials were determined from these.
Electrosynthesis of Organic Compounds. V. Electrochemical Reduction of Selected Arylalkyl Halides
Ismail, M. T.,Abdel-Wahab, A. A.,Mohamed, O. S.,Khalaf, A. A.
, p. 1174 - 1176 (2007/10/02)
Electrochemical reductions of some selected arylalkyl halides were carried out in methanol containing 0.1 mol*l-1 Ba(ClO4)2 on different cathodes (Hg, Zn).The compounds investigated were benzyl bromide (1); phenylethyl bromide (2); 3-phenylpropyl bromide (3); 4-phenylbutyl chloride (4); 1-methyl-3-phenylpropyl chloride (5); 1,1-dimethyl-3-phenylpropyl chloride (6) and 1,1-dimethyl-4-phenylbutyl chloride (7).The isolated products were found to include hydrogen abstraction, dehydrogenation, dimerization as well as cyclization products.Suitable mechanism involving the formation of intermediate carbanions and of free radicals was suggested to explain the results.Also, polarization curves for the compounds investigated were measured and the reduction half-wave potentials were determined.
Cyclophanes, XXI. The Chemical Behavior of Paracyclophane: Reactions of the Benzene Ring
Noble, Karl-Ludwig,Hopf, Henning,Ernst, Ludger
, p. 455 - 473 (2007/10/02)
Preparative quantities of paracyclophane (1b) may be prepared from paracyclophane-3,6-dione (9) by Wolff-Kishner reduction.After a detailed dicussion of the 1H and 13C NMR spectra of 1b, its behavior in substitution and addition reactions is describ
