- Desulfonylative Electrocarboxylation with Carbon Dioxide
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Electrocarboxylation of organic halides is one of the most investigated electrochemical approaches for converting thermodynamically inert carbon dioxide (CO2) into value-added carboxylic acids. By converting organic halides into their sulfone derivatives, we have developed a highly efficient electrochemical desulfonylative carboxylation protocol. Such a strategy takes advantage of CO2as the abundant C1 building block for the facile preparation of multifunctionalized carboxylic acids, including the nonsteroidal anti-inflammatory drug ibuprofen, under mild reaction conditions.
- Zhong, Jun-Song,Yang, Zi-Xin,Ding, Cheng-Lin,Huang, Ya-Feng,Zhao, Yi,Yan, Hong,Ye, Ke-Yin
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supporting information
p. 16162 - 16170
(2021/09/02)
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- Electrogenerated Sm(II)-Catalyzed CO2 Activation for Carboxylation of Benzyl Halides
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Sm(II)-catalyzed carboxylation of benzyl halides is reported through the electrochemical reduction of CO2. The transformation proceeds under mild reaction conditions to afford the corresponding phenylacetic acids in good to excellent yields. This user-friendly and operationally simple protocol represents an alternative to traditional strategies, which usually proceeds through the C(sp3)-halide activation pathway.
- Bazzi, Sakna,Schulz, Emmanuelle,Mellah, Mohamed
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supporting information
p. 10033 - 10037
(2019/12/24)
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- Silver encapsulated copper salen complex: Efficient catalyst for electrocarboxylation of cinnamyl chloride with CO2
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An active catalyst, [Cu]?Ag composite, was synthesized for the first time and used as a cathode for electrocarboxylation of cinnamyl chloride with CO2. β,γ-Unsaturated carboxylic acids were obtained with excellent yield and moderate selectivity. Moreover, reasonable yields and selectivities of carboxylic acids were also achieved with several allylic halides and aryl halides.
- Wu, La-Xia,Zhao, Ying-Guo,Guan, Ye-Bin,Wang, Hui,Lan, Yang-Chun,Wang, Huan,Lu, Jia-Xing
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p. 32628 - 32633
(2019/10/28)
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- Synthetic method of fatty acid containing nitrogen heterocycle
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The invention discloses a synthetic method of fatty acid containing nitrogen heterocycle. The synthetic method comprises the following steps: (S1) adding a heterocyclic compound with substitution of chloromethyl groups, a catalyst and a solvent DMF into a reaction kettle; (S2) introducing carbon dioxide to lead the pressure in the kettle to be 2-4MPa, adjusting and reacting for 10-16 hours at thetemperature of 40-50 DEG C; (S3) adding diluted hydrochloric acid into the reaction kettle to carry out acidification, using ethyl acetate for extraction, combining organic phases, carrying out rotaryevaporation to remove liquid, and further carrying out vacuum drying, thus obtaining the fatty acid containing nitrogen heterocycle. The synthetic method disclosed by the invention has the beneficialeffects that a one-pot method is adopted, the raw materials are easy to obtain, price is low, aftertreatment of products is also simpler, the universality for a substrate is also very high, and the promotion and application are easy.
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Paragraph 0042
(2018/07/30)
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- Palladium-Catalyzed Carboxylation of Benzyl Chlorides with Atmospheric Carbon Dioxide in Combination with Manganese/Magnesium Chloride
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An efficient direct carboxylation of a series of benzyl chlorides with CO2 catalyzed by Pd(OAc)2/dicyclohexyl (2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (SPhos) was developed to afford the corresponding phenylacetic acids in combination with Mn powder as a reducing reagent and MgCl2 as an indispensable additive. The reaction proceeded smoothly under 1 atm CO2. The application of Mn powder instead of a sensitive reducing reagent represents an operationally simple access to phenylacetic acids. Notably, MgCl2 is able to stabilize the (SPhos)2PdII(Bn)(Cl)(η1-CO2)(MgCl2) adduct and thus facilitates CO2 insertion into the PdII-C bond, which is supported by a DFT study. Specific effect: MgCl2 facilitates the direct insertion of CO2 into the PdII-C bond by stabilizing the PdII-CO2 adduct. With MgCl2 as an indispensable additive, the Pd-catalyzed carboxylation of various benzyl chlorides proceeded smoothly under 1 atm CO2, and the application of Mn powder instead of a sensitive reducing reagent makes this protocol an operationally simple access to phenylacetic acids.
- Zhang, Shuai,Chen, Wei-Qiang,Yu, Ao,He, Liang-Nian
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p. 3972 - 3977
(2016/01/26)
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- Ni-catalyzed direct carboxylation of benzyl halides with CO2
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A novel Ni-catalyzed carboxylation of benzyl halides with CO2 has been developed. The described carboxylation reaction proceeds under mild conditions (atmospheric CO2 pressure) at room temperature. Unlike other routes for similar means, our method does not require well-defined and sensitive organometallic reagents and thus is a user-friendly and operationally simple protocol for assembling phenylacetic acids.
- León, Thierry,Correa, Arkaitz,Martin, Ruben
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supporting information
p. 1221 - 1224
(2013/03/14)
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- Catalytic properties of several supported Pd(II) complexes for Suzuki coupling reactions
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Pd(II) complexes with N-ligands were synthesized and tested for Suzuki coupling reaction. These complexes were also heterogenized on silica. The resulting site-isolated catalysts showed a high catalytic activity. The most stable complex was supported N-(propyl)ethylenediamine, which did not display any notable leaching. The effects of reaction conditions and the nature of the boronic acid derivative on the conversion of the starting compounds were studied.
- Vassylyev, Oleksiy,Chen, Jengshiou,Panarello, Anthony P.,Khinast, Johannes G.
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p. 6865 - 6869
(2007/10/03)
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- Toward environmentally friendly photolithographic materials: A new class of water-soluble photoresists
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New water-soluble styrenic polymers bearing two functional groups, pendant ammonium salts of half-esters of malonic acids and acid-labile alkyl esters, were synthesized and evaluated for water-soluble positive-tone photoresist application. These polymers feature two solubility switches: insolubilization of the entire film by baking and selective solubilization upon exposure to UV light. Time-resolved FT-IR measurement of the baked films showed sequential evaporation of ammonia from the films and the decarboxylation of the malonate half-esters. The rates of decarboxylation depend on the structure of substituents at the 2-position of the malonates. The choice of acid-labile esters, the structure of the half-esters, and the polymer compositions were carefully optimized, and high-resolution positive tone images were obtained that were fully processed in aqueous media.
- Yamada, Shintaro,Mrozek, Thomas,Rager, Timo,Owens, Jordan,Rangel, Jose,Willson, C. Grant,Byers, Jeffery
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p. 377 - 384
(2007/10/03)
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- Absolute rate constants of alkene addition reactions of a fluorinated radical in water
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Absolute rate constants of ·RfSO3-radical addition to a series of water-soluble alkenes containing ionic, carboxylate substituents were measured by laser flash photolysis experiments in water. The observed rate constants w
- Zhang,Dolbier Jr.,Sheeller,Ingold
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p. 6362 - 6366
(2007/10/03)
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