120-48-9Relevant articles and documents
Esterification of carboxylic acids with alkyl halides using imidazolium based dicationic ionic liquids containing bis-trifluoromethane sulfonimide anions at room temperature
Jadhav, Arvind H.,Lee, Kyuyoung,Koo, Sangho,Seo, Jeong Gil
, p. 26197 - 26208 (2015)
Task-specific room temperature ionic liquids (RTILs) composed of symmetrical N-methylimidazolium rings linked with a short oligo (ethylene glycol) chain (cationic part) and bis-trifluoromethane sulfonimide (NTf2, anionic part) were successfully synthesized, and their physicochemical properties were determined by various modern analytical techniques. The catalytic activity of the synthesized RTILs was evaluated in the esterification reaction of acids with alkyl halides in solvent-free conditions at room temperature. From the screening test, all the synthesized RTILs showed a high yield with significant selectivity for respective esters in a very short reaction time. Especially, 0.1 equimolar of RTIL-1 ([tetraEG(mim)2][NTf2]2) was found to be, the most efficient and reusable catalyst for this reaction. As a result, 100% conversion and up to a 94% yield of the respective ester product was obtained in a 30 min reaction time. This might be due to their synergetic effect of Lewis acidity, wide liquid range, and high miscibility compared to the other homogeneous and heterogeneous catalysts. Beside this, RTIL was easily separated from the reaction mixture and reused several times without any significant loss of catalytic activity and structural property. The present dicationic ionic liquids (ILs) under a solvent-free catalytic system were found to be kinetically fast, naturally benign, and achieved good yields for esterification of carboxylic acids with alkyl halides.
Fe2(SO4)3·xH2O in synthesis: A convenient and efficient catalyst for the esterification of aromatic carboxylic acids with alcohols
Zhang, Gui-Sheng
, p. 607 - 611 (1999)
Fe2(SO4)3·xH2O has been used for the catalyst in the esterification of aromatic carboxylic acids with alcohols. The method offers mild reaction condition, easy work-up, and high yields of the esterification products.
Butoxycarbonylation of aryl halides catalyzed by a silica-supported poly[3-(2-cyanoethylsulfanyl)propylsiloxane palladium] complex
Cai, Ming-Zhong,Song, Cai-Sheng,Huang, Xian
, p. 2273 - 2274 (1997)
Aryl bromides and iodides react with carbon monoxide and n-butyl alcohol at 100°C and atmospheric pressure in the presence of tri-n-butylamine and a catalytic amount of a silica-supported sulfur palladium complex to form esters in moderate to good yields.
Mechanistic insight into the synergistic Cu/Pd-catalyzed carbonylation of aryl iodides using alcohols and dioxygen as the carbonyl source
Li, Junxuan,Zhou, Jinlei,Wang, Yumei,Yu, Yue,Liu, Qiang,Yang, Tilong,Chen, Huoji,Cao, Hua
, p. 68 - 74 (2021/11/16)
Pd-catalyzed carbonylation, as an efficient synthetic approach to the installation of carbonyl groups in organic compounds, has been one of the most important research fields in the past decade. Although elegant reactions that allow highly selective carbonylations have been developed, straightforward routes with improved reaction activity and broader substrate scope remain long-term challenges for new practical applications. Here, we show a new type of synergistic Cu/Pd-catalyzed carbonylation reaction using alcohols and dioxgen as the carbonyl sources. A broad range of aryl iodides and alcohols are compatible with this protocol. The reaction is concise and practical due to the ready availability of the starting materials and the scalability of the reaction. In addition, the reaction affords lactones and lactams in an intermolecular fashion. Moreover, DFT calculations have been performed to study the detailed mechanisms. [Figure not available: see fulltext.]
Encapsulation of heteropolyacids within hollow microporous polymer nanospheres for sustainable esterification reaction
He, Zhiwei,Huang, Kun,Song, Chunmei,Wang, Huaqing,Yu, Haitao,Zhang, Li
, (2021/10/25)
Herein, the Keggin structural phosphotungstic acid (HPW) has been successfully encapsulated within hollow microporous polymer nanospheres (H-MPNs) by a “ship-in-bottle” approach. The H-MPNs are formed by self-assembly induced by hyper-crosslinking of polylactide-b-polystyrene (PLA-b-PS). The obtained catalysts (HPW@H-MPNs) exhibit more sustainable availability than the previously reported HPW-supported catalysts in esterification reaction. This excellent sustainability can be attributed to the stable microporous channels in H-MPNs which are smaller than the molecular size of HPW, thereby effectively preventing the HPW from leaking out. Moreover, such catalysts also perform well in terms of catalytic activity and universality because of the combination of a hollow structure in the interior and permeable pore channels in the shells. This type of polymer carrier and general encapsulation method may provide a new strategy for developing more sustainable catalysts for various chemical reactions.
Carboxyboronate as a Versatile In Situ CO Surrogate in Palladium-Catalyzed Carbonylative Transformations
Tien, Chieh-Hung,Trofimova, Alina,Holownia, Aleksandra,Kwak, Branden S.,Larson, Reed T.,Yudin, Andrei K.
supporting information, p. 4342 - 4349 (2020/12/25)
The application of carboxy-MIDA-boronate (MIDA=N-methyliminodiacetic acid) as an in situ CO surrogate for various palladium-catalyzed transformations is described. Carboxy-MIDA-boronate was previously shown to be a bench-stable boron-containing building block for the synthesis of borylated heterocycles. The present study demonstrates that, in addition to its utility as a precursor to heterocycle synthesis, carboxy-MIDA-boronate is an excellent in situ CO surrogate that is tolerant of reactive functionalities such as amines, alcohols, and carbon-based nucleophiles. Its wide functional-group compatibility is highlighted in the palladium-catalyzed aminocarbonylation, alkoxycarbonylation, carbonylative Sonogashira coupling, and carbonylative Suzuki–Miyaura coupling of aryl halides. A variety of amides, esters, (hetero)aromatic ynones, and bis(hetero)aryl ketones were synthesized in good-to-excellent yields in a one-pot fashion.
