- Method for preparing aromatic carboxylic acid compound
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The invention discloses a method for preparing an aromatic carboxylic acid compound. The method comprises the following steps: 1) heating carbon dioxide and hydrosilane in the presence of a copper catalyst in a reaction medium A; and 2) adding a reaction medium B, aryl halide, a palladium catalyst and a base to the reaction mixture in the step 1), sealing the reaction system, and performing a heating reaction. The method has the advantages that raw materials are simple and easy to obtain, the raw materials are cheap and stable, the catalyst is common, easy to obtain and stable, the reaction conditionsaremild, the aftertreatment is simple, the yield is high, and the like.
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Paragraph 0085-0086; 0128-0131; 0176
(2020/02/14)
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- Convenient synthesis of 3-Hydroxyquinolines via dakin oxidation: A short synthesis of Jineol
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A convenient synthesis of 3-hydroxyquinolines has been described via unprecedented Dakin oxidation of quinoline-3-carboxaldehydes. Subsequently, application of the methodology to a high yielding synthesis of quinoline alkaloid Jineol (1) is reported.
- Ghorai, Sujit K.,Dasgupta, Mayukh,Dutta, Piyali,Dumeunier, Raphael,Mal, Sanjib,Patre, Rupesh,Kuilya, Tapan Kumar,Pal, Sitaram,Manjunath, Bhanu N.
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supporting information
(2020/08/06)
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- Nickel-catalyzed carboxylation of aryl and heteroaryl fluorosulfates using carbon dioxide
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The development of efficient and practical methods to construct carboxylic acids using CO2 as a C1 synthon is of great importance. Nickel-catalyzed carboxylation of aryl fluorosulfates and heteroaryl fluorosulfates with CO2 is described, affording arene carboxylic acids with good to excellent yields under mild conditions. In addition, a one-pot phenol fluorosulfation/carboxylation is developed.
- Ma, Cong,Zhao, Chuan-Qi,Xu, Xue-Tao,Li, Zhao-Ming,Wang, Xiang-Yang,Zhang, Kun,Mei, Tian-Sheng
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p. 2464 - 2467
(2019/04/10)
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- Tandem one-pot CO2 reduction by PMHS and silyloxycarbonylation of aryl/vinyl halides to access carboxylic acids
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The present study discloses the synthesis of aryl/vinyl carboxylic acids from Csp2-bound halides (Cl, Br, I) in a carbonylative path by using silyl formate (from CO2 and hydrosilane) as an instant CO-surrogate. Hydrosilane provides hydride for reduction and its oxidation product silanol serves as a coupling partner. Mono-, di-, and tri-carboxylic acids were obtained from the corresponding aryl/vinyl halides.
- Paridala, Kumaraswamy,Lu, Sheng-Mei,Wang, Meng-Meng,Li, Can
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supporting information
p. 11574 - 11577
(2018/10/31)
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- Carboxylation of Aromatic and Aliphatic Bromides and Triflates with CO2 by Dual Visible-Light–Nickel Catalysis
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We report the efficient carboxylation of bromides and triflates with K2CO3 as the source of CO2 in the presence of an organic photocatalyst in combination with a nickel complex under visible light irradiation at room temperature. The reaction is compatible with a variety of functional groups and has been successfully applied to the synthesis and derivatization of biologically active molecules. In particular, the carboxylation of unactivated cyclic alkyl bromides proceeded well with our protocol, thus extending the scope of this transformation. Spectroscopic and spectroelectrochemical investigations indicated the generation of a Ni0 species as a catalytic reactive intermediate.
- Meng, Qing-Yuan,Wang, Shun,K?nig, Burkhard
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supporting information
p. 13426 - 13430
(2017/10/07)
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- Effective palladium-catalyzed hydroxycarbonylation of aryl halides with substoichiometric carbon monoxide
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A protocol for the Pd-catalyzed hydroxycarbonylation of aryl iodides, bromides, and chlorides has been developed using only 1-5 mol % of CO, corresponding to a pCO as low as 0.1 bar. Potassium formate is the only stoichiometric reagent, acting as a mildly basic nucleophile and a reservoir of CO. The substoichiometric CO could be delivered to the reaction from an acyl-Pd(II) precatalyst, which provides both the CO and an active catalyst, and thereby obviates the need for handling a toxic gas.
- Korsager, Signe,Taaning, Rolf H.,Skrydstrup, Troels
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supporting information
p. 2891 - 2894
(2013/04/10)
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- Preparation of 4,7-diphenyl-1,10-phenanthroline-2,9-dicarboxylic acid catalyzed by iron(III)porphyrins with (diacetoxyiodo)benzene
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Using iron(III)porphyrins in combination with (diacetoxyiodo)benzene allows for the conversion of 2,9-bis(bromomethyl)-4,7-diphenyl-1,10-phenanthroline into 4,7-diphenyl-1,10-phenanthroline-2,9-dicarboxylic acid. This method provides a cost-effective and environmentally-friendly oxidation procedure using less toxic PhI(OAc)2 and biologically relevant iron(III)porphyrins. The catalytic activity of five kinds of iron-metallated functional porphyrins were investigated using different oxidants, including air, H2O 2, PhI(OAc)2, PhIO and NaClO. Our results showed that the use of T(p-NO2)PPFeCl with PhI(OAc)2 as the oxidant in the presence of water displays remarkable activity for the desired oxidation reaction. The generality of this method was examined by synthesizing the carboxylic acids of pyridines and quinolines.
- Zhong, Qi-Di,Xue, Yun-Zhou,Yan, Hong,Song, Xiu-Qing,Zhong, Ru-Gang
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body text
p. 5532 - 5535
(2010/12/20)
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- Palladium-catalyzed aminocarbonylation of heteroaryl halides using di-tert-butylphosphinoferrocene
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Pd-catalyzed aminocarbonylation of heteroaryl halides, using monodentate ligand di-tert-butylphosphinoferrocene tetrafluoroborate is reported. Good to high yields were obtained with chiral amines on a variety of substrates including 2-bromo heteroaryls.
- Qu, Bo,Haddad, Nizar,Han, Zhengxu S.,Rodriguez, Sonia,Lorenz, Jon C.,Grinberg, Nelu,Lee, Heewon,Busacca, Carl A.,Krishnamurthy, DhileepKumar,Senanayake, Chris H.
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experimental part
p. 6126 - 6129
(2010/01/18)
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- Synthesis and reactivity of lithium tri(quinolinyl)magnesates
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2-, 3- and 4-Bromoquinolines were converted to the corresponding lithium tri(quinolinyl)magnesates at -10°C when exposed to Bu3MgLi in THF. The resulting organomagnesium derivatives were quenched with various electrophiles or involved in metal-catalyzed coupling reactions with heteroaryl halides to afford functionalized quinolines.
- Dumouchel, Sylvain,Mongin, Florence,Trécourt, Fran?ois,Quéguiner, Guy
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p. 8629 - 8640
(2007/10/03)
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- CATALYSTS COMPRISING N-SUBSTITUTED CYCLIC IMIDES AND PROCESSES FOR PREPARING ORGANIC COMPOUNDS WITH THE CATALYSTS
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A catalyst of the invention includes an imide compound having a N-substituted cyclic imide skeleton represented by following Formula (I): wherein R is a hydroxyl-protecting group. Preferred R is a hydrolyzable protecting group. R may be a group obtained from an acid by eliminating an OH group therefrom. Such acids include, for example, carboxylic acids, sulfonic acids, carbonic acid, carbamic acid, sulfuric acid, nitric acid, phosphoric acids and boric acids. The catalyst may include the imide compound and a metallic compound in combination. In the presence of the catalyst, (A) a compound capable of forming a radical is allowed to react with (B) a radical scavenging compound and thereby yields an addition or substitution reaction product of the compound (A) and the compound (B) or a derivative thereof. This catalyst can produce an organic compound with a high selectivity in a high yield as a result of, for example, an addition or substitution reaction under mild conditions.
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- Remarkable effect of nitrogen dioxide for N-hydroxyphthalimide-catalyzed aerobic oxidation of methylquinolines
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Aerobic oxidation of methylquinolines was successfully achieved by the use of N-hydroxyphthalimide/Co(OAc)2/Mn(OAc)2 as catalyst in the presence of a small amount of nitrogen dioxide as an initiator.
- Sakaguchi, Satoshi,Shibamoto, Akihiro,Ishii, Yasutaka
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p. 180 - 181
(2007/10/03)
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- Biocatalytic oxidation of 2-methylquinoxaline to 2-quinoxalinecarboxylic acid
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A microbial process using the fungus Absidia repens ATCC 14849 is described for the oxidation of 2-methylquinoxaline to 2-quinoxalinecarboxylic acid. A campaign consisting of three 14000-L runs produced 20.5 kg of the acid with a 28% overall yield. The bioconversion gave a lower yield compared with a three step chemical synthesis (35%), but was carried out in one pot, and avoided safety issues with a di-N-oxide intermediate. Although successfully scaled to produce kilograms of 2-quinoxalinecarboxylic acid for synthesis of a drug candidate, the A. repens bioconversion is unsuitable for further scale-up due to low product concentration (～1 g/L). A second microbial process using Pseudomonas putida ATCC 33015 is also described for the oxidation of 2-methylquinoxaline. The P. putida bioconversion gave an 86% in situ yield at 8-L scale and yielded a product concentration approximately 10-fold greater than that of the A. repens bioconversion.
- Wong, John W.,Watson Jr., Harry A.,Bouressa, James F.,Burns, Michael P.,Cawley, James J.,Doro, Albert E.,Guzek, Donald B.,Hintz, Michael A.,McCormick, Ellen L.,Scully, Douglas A.,Siderewicz, Joseph M.,Taylor, William J.,Truesdell, Susan J.,Wax, Richard G.
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p. 477 - 481
(2013/09/06)
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- A mild and convenient procedure for the oxidation of aromatic aldehydes to carboxylic acids using urea-hydrogen peroxide in formic acid
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Mild and safe oxidation of aromatic and heteroaromatic aldehydes to the corresponding acids was achieved by using UHP in formic acid.
- Balicki
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p. 2195 - 2198
(2007/10/03)
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- An in-depth study of the biotransformation of nitriles into amides and/or acids using Rhodococcus rhodochrous AJ270
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A variety of aliphatic, aromatic and heterocyclic nitriles have been readily hydrolysed into the corresponding amides and/or acids under very mild conditions using Rhodococcus sp. AJ270. The nitrile hydratase involved in this novel nitrile-hydrolysing microorganism efficiently hydrates most nitriles tested, irrespective of the electronic and steric effects of the substituents, to form the amides. Conversion of amides into acids catalysed by the associated amidase is rapid and efficient in most cases. Substrates bearing an adjacent substituent (which may be an ortho substituent on an aromatic nitrile, an adjacent heteroatom in a heterocyclic ring or a geminal substituent in an α,β-unsaturated nitrile) undergo slow hydrolysis of the amides allowing efficient amide isolation. The scope, limitations and reaction mechanism of this enzymatic process have been systematically studied. A molecular size of >7 A diameter and the presence of functions capable of metal complexation near to the nitrile inhibit hydrolysis.
- Meth-Cohn, Otto,Wang, Mei-Xiang
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p. 1099 - 1104
(2007/10/03)
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- A Powerful New Nitrile Hydratase For Organic Synthesis-Aromatic And Heteroaromatic Nitrile Hydrolyses- A Rationalisation
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A powerful new nitrile hydratase organism, Rhodococcus rhodocrous AJ270 has been isolated that efficiently hydrolyses all kinds of nitriles to amides and/or acids.This paper shows that aromatic and heterocyclic nitriles are readily hydrolysed to acids but, that those bearing an adjacent-substituent (which may be an ortho substituent or an adjacent heteroatom in the ring) give amides in good yield but only slowly proceed to acids.
- Meth-Cohn, Otto,Wang, Mei-Xiang
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p. 9561 - 9564
(2007/10/02)
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- Photochemical Reaction of Ethoxycarbonyl-Substituted Quinolines
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The photochemical reactions of the quinoline derivatives substituted by an ethoxycarbonyl group at the 2-, 3-, and 4-positions of a quinoline nucleus have been investigated in several alcohols and cyclohexane.Irradiation of ethyl 4-quinolinecarboxylate (1) yielded ethyl 2-hydroxyalkyl-4-quinolinecarboxylates (4a-c) in alcohols and ethyl 2-cyclohexyl-4-quinolinecarboxylate (4d) in cyclohexane in a good yield, respectively.The photochemical reactions of ethyl 3-quinolinecarboxylate (2) showed remarkable solvent dependency.Irradiation in methanol and cyclohexane afforded a solvent-additive product, ethyl 4-hydroxymethyl-1,4-dihydro-3-quinolinecarboxylate (5a) and ethyl 4-cyclohexyl-1,4-dihydro-3-quinolinecarboxylate (5b), while such photoaddition of the solvent did not proceed in ethanol and 2-propanol but instead ethyl 1,4-dihydro-3-quinolinecarboxylate (6) and dimeric compounds were formed, both of which were unstable and finally reverted to 2 at room temperature in air.In the case of ethyl 2-quinolinecarboxylate two types of the products, ethyl 4-hydroxyalkyl-1,4-dihydro-2-quinolinecarboxylate (7) and ethyl 1,4-dihydro-2-quinolinecarboxylate (8) were obtained in ethanol and 2-propanol but the yields of those products were poor.On the basis of triplet quenching experiments, the photochemical reactions of those ethyl quinolinecarboxylates are suggested to occur through hydrogen abstraction from the solvents by the ring nitrogen in the S1 state.
- Ono, Isao,Hata, Norisuke
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p. 2891 - 2898
(2007/10/02)
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