60200-91-1Relevant academic research and scientific papers
Palladium-Catalyzed Enantioselective C(sp3)-H Arylation of 2-Propyl Azaaryls Enabled by an Amino Acid Ligand
Antilla, Jon C.,Jing, Hua-Qing,Kuninobu, Yoichiro,Li, Hong-Liang,Yang, Deng-Feng
, p. 1286 - 1291 (2022/02/25)
A palladium(II)-catalyzed enantioselective arylation of unbiased secondary C(sp3)-H bonds was developed. The enantioselectivity was controlled by the combination of a pyridyl or isoquinolinyl directing group and an amino acid, N-Boc-2-pentyl proline. A variety of 2-propyl azaaryls and biaryl iodides were employed to provide arylated products in moderate to good yields (up to 82%) with high enantioselectivities (up to 93:7 er). This reaction is a rare example of an amino-acid-enabled enantioselective acyclic methylene C(sp3)-H arylation. Furthermore, the reaction proceeded with high enantioselectivity even on a gram scale, and the product was transformed to a 5,6,7,8-tetrahydroisoquinoline bioactive molecule. Kinetic isotope effect (KIE) experiments indicated that C-H activation is the rate-determining step for the enantioselective C(sp3)-H arylation.
Palladium-Catalyzed Secondary C(sp3)?H Arylation of 2-Alkylpyridines
Li, Hong-Liang,Kuninobu, Yoichiro
, p. 2637 - 2641 (2020/06/02)
A pyridyl group-assisted palladium-catalyzed secondary C(sp3)?H arylation protocol was developed. A substituent at the 3-position of the pyridyl group is proved to be important for promoting C?H arylation and controlling the regioselectivity. Aryl iodides can be used as coupling partners. The reaction proceeded in good to excellent yields with good functional group tolerance, even on the gram-scale. The preliminary asymmetric reaction was investigated using an L-proline derivative as a chiral ligand. (Figure presented.).
The chlorinated aromatic iodine compound method
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Paragraph 0050, (2017/05/12)
PROBLEM TO BE SOLVED: To provide an industrially advantageous production method that makes it possible to produce aromatic chloroiodine compounds.SOLUTION: A production method of an aromatic chloroiodine compound is characterized by making an aromatic iodine compound and a sulfuryl chloride react with each other in the presence of a specific Lewis acid catalyst and a sulfur compound.
Synthesis of functionalized thiophene/phenyl co-oligomers by direct arylation of thiophenes
Osadnik, Andreas,Lützen, Arne
, p. 40 - 51 (2015/02/19)
π-Conjugated rod-like molecules have proven to be powerful candidates for the generation of well-defined nanostructures with interesting optical and optoelectrical properties. Their synthesis, however, turns out to be rather complex in some cases. Here, we have optimized the synthesis of oligomers consisting of thiophene and phenylene groups with three or four aromatic units using a direct arylation approach, which allows us to use cheap starting materials and to minimize the number of reaction steps considerably.
Synthesis and antiplasmodial activity of new indolone N-Oxide derivatives
Nepveu, Fran?oise,Kim, Sothea,Boyer, Jeremie,Chatriant, Olivier,Ibrahim, Hany,Reybier, Karine,Monje, Marie-Carmen,Chevalley, Severine,Perio, Pierre,Lajoie, Barbora H.,Bouajila, Jalloul,Deharo, Eric,Sauvain, Michel,Tahar, Rachida,Basco, Leonardo,Pantaleo, Antonella,Turini, Francesco,Arese, Paolo,Valentin, Alexis,Thompson, Eloise,Vivas, Livia,Petit, Serge,Nallet, Jean-Pierre
experimental part, p. 699 - 714 (2010/07/09)
A series of 66 new indolone-N-oxide derivatives was synthesized with three different methods. Compounds were evaluated for in vitro activity against CQ-sensitive (3D7), CQ-resistant (FcB1), and CQ and pyrimethamine cross-resistant (K1) strains of Plasmodium falciparum (P.f.), aswell as for cytotoxic concentration (CC50) on MCF7 and KB human tumor cell lines. Compound 26 (5-methoxy-indolone-N-oxide analogue) had the most potent antiplasmodial activity in vitro (50 MCF7/IC50 FcB1: 14623; CC50 KB/IC50 3D7: 198823). In in vivo experiments, compound 1 (dioxymethylene derivatives of the indolone-N-oxide) showed the best antiplasmodial activity against Plasmodium berghei, 62% inhibition of the parasitaemia at 30 mg/kg/day. 2009 American Chemical Society.
Synthesis of monofunctionalized p-quaterphenyls
Wallmann, Ivonne,Schiek, Manuela,Koch, Rainer,Luetzen, Arne
scheme or table, p. 2446 - 2450 (2009/04/11)
p-Oligophenyls have proven to be versatile building blocks for the generation of self-assembled nanoaggregates via vapor deposition on solid supports whose optical properties and morphologies can be influenced by the introduction of functional groups. Non
Synthesis of symmetrically and unsymmetrically para-functionalized p-quaterphenylenes
Schiek, Manuela,Al-Shamery, Katharina,Luetzen, Arne
, p. 613 - 621 (2008/01/04)
Oligo-p-phenylenes have proven to be versatile building blocks for the generation of self-assembled nanoaggregates with interesting optical properties via vapor deposition on solid supports. Preliminary studies have shown that both the properties and the morphologies of these aggregates can be influenced by the introduction of functional groups. To this end, we have developed general approaches to the synthesis of symmetrically and unsymmetrically 1,4?-substituted p-quaterphenylenes through the application of a reliable Suzuki cross-coupling strategy. Georg Thieme Verlag Stuttgart.
Silicon directed ipso-substitution of polymer bound arylsilanes: Preparation of biaryls via the Suzuki cross-coupling reaction
Han, Yongxin,Walker, Shawn D.,Young, Robert N.
, p. 2703 - 2706 (2007/10/03)
A method for attaching haloarylsilanes to polymer support was developed. The polymer bound arylhalide were reacted with a variety of ArB(OH)2 under the Suzuki cross-coupling reaction conditions and the coupled resins were cleaved by different electrophiles to give ipso-substitution products in good yields.
Analogues of clofibrate and clobuzarit containing fluorine in the side chains
Haydock,Mulholland,Telford,et al.
, p. 205 - 214 (2007/10/02)
A series of analogues of clofibrate and 2-[4-(4-chlorophenyl)phenylmethoxy]-2-methylpropionic acid (clobuzarit) has been prepared by replacing the methyl groups by trifluoromethyl groups and changing the aromatic moiety. The activity of these compounds has been assayed on the plasma levels of cholesterol, Total Esterified Fatty Acids (T.E.F.A.) and fibrinogen in rats. It appears that derivatives of the first series which contain only one trifluoromethyl group are hypocholesterolaemic and that many mono- of bis- trifluoromethyl derivatives of the second series lower the levels of both cholesterol and T.E.F.A. in contrast to clobuzarit.
Aryl radicals from hexazadienes and tetrazenes
Mackay, Donald,McIntyre, Deane Douglas
, p. 990 - 999 (2007/10/02)
Aryl radicals are produced from both ends of the hexazadienes 1 and 2 and from the tetrazene 3, either thermally or photolytically.They attack aromatic compounds in the nucleus, the yield of biaryl being in the range 40-70percent, though it can be made nearly quantitative by using m-dinitrobenzene as additive.The aryl radicals also oxidize 2-propanol to acetone, the reaction products being the halogenobenzene and 1,2-diacetylhydrazine.Photolysis of 1 goes mainly by way of the tetrazene 3, and this may also be a significant pathway in the thermal reaction.Azodiacetylis an intermediate in the thermal reaction of 1 with 2-propanol and may be generally so in all its reactions.Radical induced decomposition is believed to be important in the reactions of 1, 2, and 3, and it is probably responsible for the formation of 1-acetyl-1-arylhydrazines, routinely produced in yields up to 25percent.
