1575-96-8Relevant academic research and scientific papers
cis-BIS(7-METHYLNAPHTH-1-YL)BIS(TRIPHENYLPHOSPHAN)PLATIN(II)
Brune, Hans Albert,Schaefer, Wolfgang,Spohn, Karl-Heinz,Weisemann, Claus
, p. 367 - 376 (1986)
From the reaction of cis-dichlorbis(triphenylphosphane)platinum(II) with the lithium compound obtained as the bromination product of 2-methylnaphthalene cis-bis(7-metyhylnaphth-1-yl)bis(triphenylphosphane)platinum(II) (6), has been isolated.The unexpected formation of 6 has been explained.
Lewis acid-mediated carboxylation of fused aromatic compounds with carbon dioxide
Suzuki, Yutaka,Hattori, Tetsutaro,Okuzawa, Tomohiro,Miyano, Sotaro
, p. 102 - 103 (2002)
Direct and regioselective carboxylation of fused aromatic compounds with carbon dioxide is achieved with the aid of a Lewis acid. Thus, treatment of naphthalene, anthracene, and phenanthrene with carbon dioxide (3.0 MPa) in benzene at 40 °C in the presenc
Controlling chemoselectivity in reactions of unprotected naphthalene-1-carboxylic acid with strong bases
Tilly, David,Castanet, Anne-Sophie,Mortier, Jacques
, p. 446 - 447 (2005)
Whereas treatment of unprotected naphthalene-1-carboxylic acid with alkyllithiums (RLi) affords 1,4-addition products, the reaction with LTMP/Me3SiCl under in situ quench conditions provides the arylsilane arising out from the substitution of l
Palladium-Catalyzed ortho-C-H Methylation of Benzoic Acids
Lv, Weiwei,Wen, Si,Liu, Jing,Cheng, Guolin
, p. 9786 - 9791 (2019/08/26)
A palladium-catalyzed methylation of C-H bonds of benzoic acids with di-tert-butyl peroxide as the methylating reagent under an external oxidant and ligand-free conditions has been achieved. The reaction is found to be directed by a weakly coordinating carboxyl group, offering a facile route for the synthesis of highly functionalized ortho-methyl benzoic acids.
Site- and regio-selective incorporation of carbon dioxide into the C(sp2)Si bond of benzosilacyclobutenes
Ishida, Naoki,Okumura, Shintaro,Murakami, Masahiro
, p. 570 - 572 (2018/04/12)
A reaction of benzosilacyclobutenes with carbon dioxide is catalyzed by a nickel complex having an N-heterocyclic carbene ligand. Carbon dioxide inserts into the C(sp2)Si bond in a site- and regio-selective manner to form a carboncarbon bond, furnishing benzoic acid derivatives.
Iron-Catalyzed Ortho C-H Methylation of Aromatics Bearing a Simple Carbonyl Group with Methylaluminum and Tridentate Phosphine Ligand
Shang, Rui,Ilies, Laurean,Nakamura, Eiichi
supporting information, p. 10132 - 10135 (2016/08/31)
Iron-catalyzed C-H functionalization of aromatics has attracted widespread attention from chemists in recent years, while the requirement of an elaborate directing group on the substrate has so far hampered the use of simple aromatic carbonyl compounds such as benzoic acid and ketones, much reducing its synthetic utility. We describe here a combination of a mildly reactive methylaluminum reagent and a new tridentate phosphine ligand for metal catalysis, 4-(bis(2-(diphenylphosphanyl)phenyl)phosphanyl)-N,N-dimethylaniline (Me2N-TP), that allows us to convert an ortho C-H bond to a C-CH3 bond in aromatics and heteroaromatics bearing simple carbonyl groups under mild oxidative conditions. The reaction is powerful enough to methylate all four ortho C-H bonds in benzophenone. The reaction tolerates a variety of functional groups, such as boronic ester, halide, sulfide, heterocycles, and enolizable ketones.
Direct Carboxylation of Aryl Tosylates by CO2 Catalyzed by in situ-Generated Ni0
Rebih, Fatima,Andreini, Manuel,Moncomble, Aurlien,Harrison-Marchand, Anne,Maddaluno, Jacques,Durandetti, Muriel
, p. 3758 - 3763 (2016/03/08)
A novel Ni0-catalyzed carboxylation of aryl tosylates with carbon dioxide has been achieved under moderate temperatures and atmospheric pressure. In this procedure, the active Ni0 species is generated in situ by simply mixing the Ni0 precatalyst [NiBr2(bipy)] with an excess of manganese metal. This approach requires neither a glove-box nor the tedious preparation of sophisticated intermediate organometallic derivatives. This mild, convenient, and user-friendly process is successfully applied to the valorization of carbon dioxide and the synthesis of versatile reactants with broad tolerance of substituents.
Aryllithiums with increasing steric crowding and lipophilicity prepared from chlorides in diethyl ether. the first directly prepared room-temperature-stable dilithioarenes
Screttas, Constantinos G.,Steele, Barry R.,Micha-Screttas, Maria,Heropoulos, Georgios A.
supporting information, p. 5680 - 5683 (2013/01/15)
A convenient procedure has been developed for the preparation of synthetically useful, room-temperature-stable aryllithiums starting from aryl chlorides and lithium metal. The method provides a route to aryllithiums which have previously not been accessible cleanly or could only be prepared by using more expensive starting materials.
Optimization of isochromanone based urotensin II receptor agonists
Lehmann, Fredrik,Currier, Erika A.,Olsson, Roger,Ma, Jian-Nong,Burstein, Ethan S.,Hacksell, Uli,Luthman, Kristina
experimental part, p. 4844 - 4854 (2010/08/06)
A series of novel isochromanone based urotensin II receptor agonists have been synthesized and evaluated for their activity using a functional cell based assay (R-SAT). Several potent and efficacious derivatives were identified with 3-(3,4-dichlorophenyl)-6,7-dimethyl-3-(2-dimethylaminoethyl)isochroman-1-one (28) being the most potent compound showing an EC50-value of 51 nM, thereby being the most potent compound so far within the isochromanone series. In addition, two other heterocyclic systems (isochromanes and tetrahydroisoquinolinones) were investigated and these derivatives were found to be both potent and efficacious. The activity of the isochromane derivatives implies that the carbonyl group of the isochromanone is not necessary for activity. Furthermore it was found that the geometry of the heterocycles was more important for receptor interaction than the composition of the heteroatoms present.
Direct carboxylation of arenes and halobenzenes with CO2 by the combined use of AlBr3 and R3SiCl
Nemoto, Koji,Yoshida, Hiroki,Egusa, Naoki,Morohashi, Naoya,Hattori, Tetsutaro
experimental part, p. 7855 - 7862 (2011/02/21)
The Lewis acid-mediated direct carboxylation of aromatic compounds with CO2 is efficiently promoted by the addition of silyl chlorides bearing three alkyl and/or aryl substituents in total on the silicon atom. Thus, toluene, xylenes, mesitylene, and some other alkylbenzenes are treated with a 1:1 mixture of AlBr3 and Ph3SiCl in neat substrates under CO2 pressure (3.0 MPa) at room temperature, to give the corresponding carboxylic acids in 60-97% yields, based on AlBr3. Polycyclic arenes, including naphthalene, phenanthrene, and biphenyl, are regioselectively carboxylated in 91-98% yields with the aid of 1 molar equiv of AlBr3 and Ph3SiCl in an appropriate solvent, chosen from benzene, chlorobenzene, and fluorobenzene. These solvents, as well as bromobenzene, resist carboxylation; however, they are also carboxylated in moderate yields when treated with a 1:5 mixture of AlBr3 and iPrSiCl at elevated temperatures. The FT-IR spectrum of a mixture prepared by exposing a suspension of AlBr3 and Ph3SiCl in cyclohexane to CO 2 exhibits an absorption band around 1650 cm-1, assigned to the C=O stretching vibration of a species consisting of CO2, AlBr3, and Ph3SiCl, which suggests that the silyl chlorides activate CO2 in cooperation with AlBr3. 1H NMR analysis of unworked-up reaction mixtures reveals that the products merge as aluminum carboxylates. The mass balance concerning silicon indicates that the silyl chlorides are recycled during the reaction sequence. On the basis of these observations, a feasible mechanism is proposed for the present carboxylation.
