65853-67-0Relevant articles and documents
Mechanically induced solvent-free esterification method at room temperature
Zheng, Lei,Sun, Chen,Xu, Wenhao,Dushkin, Alexandr V.,Polyakov, Nikolay,Su, Weike,Yu, Jingbo
, p. 5080 - 5085 (2021/02/05)
Herein, we describe two novel strategies for the synthesis of esters, as achieved under high-speed ball-milling (HSBM) conditions at room temperature. In the presence of I2 and KH2PO2, the reactions afford the desired esterification derivatives in 45% to 91% yields within 20 min of grinding. Meanwhile, using KI and P(OEt)3, esterification products can be obtained in 24% to 85% yields after 60 min of grinding. In addition, the I2/KH2PO2 protocol was successfully extended to the late-stage diversification of natural products showing the robustness of this useful approach. Further application of this method in the synthesis of inositol nicotinate was also discussed. This journal is
Transition-Metal-Free DMAP-Mediated Aromatic Esterification of Amides with Organoboronic Acids
Guo, Jiarui,Liu, Lantao,Wang, Tao,Wang, Yanqing,Xu, Kai,Zhang, Yuheng
supporting information, p. 3274 - 3277 (2021/06/26)
A new, transition-metal-free, effective method for aromatic esterification of amides with organoboronic acids has been developed. A wide range of benzoate derivatives were obtained with yields ranging from moderate to good. The catalytic reaction shows a broad substrate scope and excellent functional group tolerance. Conceptually, DMAP mediates the reaction and is crucial for this transformation.
Radical Decarboxylative Carbometalation of Benzoic Acids: A Solution to Aromatic Decarboxylative Fluorination
Xu, Peng,López-Rojas, Priscila,Ritter, Tobias
supporting information, p. 5349 - 5354 (2021/05/05)
Abundant aromatic carboxylic acids exist in great structural diversity from nature and synthesis. To date, the synthetically valuable decarboxylative functionalization of benzoic acids is realized mainly by transition-metal-catalyzed decarboxylative cross couplings. However, the high activation barrier for thermal decarboxylative carbometalation that often requires 140 °C reaction temperature limits both the substrate scope as well as the scope of suitable reactions that can sustain such conditions. Numerous reactions, for example, decarboxylative fluorination that is well developed for aliphatic carboxylic acids, are out of reach for the aromatic counterparts with current reaction chemistry. Here, we report a conceptually different approach through a low-barrier photoinduced ligand to metal charge transfer (LMCT)-enabled radical decarboxylative carbometalation strategy, which generates a putative high-valent arylcopper(III) complex, from which versatile facile reductive eliminations can occur. We demonstrate the suitability of our new approach to address previously unrealized general decarboxylative fluorination of benzoic acids.
Ester Transfer Reaction of Aromatic Esters with Haloarenes and Arenols by a Nickel Catalyst
Inayama, Naomi,Isshiki, Ryota,Muto, Kei,Yamaguchi, Junichiro
, p. 3490 - 3494 (2020/03/23)
A catalytic ester transfer reaction of aromatic esters with aryl halides/arenols was developed. The present reaction can transfer an ester functional group from certain aromatic esters to haloarenes. This ester transfer reaction involves two oxidative additions-one from the C-C bond of the aromatic ester and one from the C-halogen bond of haloarenes-onto a nickel catalyst. The utilization of a Ni/dcypt catalyst capable of cleaving both chemical bonds was a key for the reaction progress. Furthermore, naphthol-based aryl electrophiles were also applicable to the catalytic system via C-O bond activation.
Choline Hydroxide as a Versatile Medium for Catalyst-Free O-Functionalization of Phenols
Joo, Seong-Ryu,Kim, Seung-Hoi,Kwon, Gyu-Tae,Park, Soo-Youl
, p. 1200 - 1205 (2020/11/30)
A versatile synthetic protocol for benzyl phenyl ether preparation via O-alkylation of phenolic oxygen with readily available benzyl derivatives was demonstrated. The newly designed procedure was carried out using an eco-friendly medium, room-temperature ionic liquid (choline hydroxide), under metal- and base-catalyst-free aerobic conditions. The reaction platform was also successfully applied to phenol protection strategy.
Method for preparing diaryl ester compound through efficient catalysis of pyridine palladium
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Paragraph 0016-0020; 0031-0035, (2020/12/31)
The invention discloses a method for preparing a diaryl ester compound through efficient catalysis of pyridine palladium. The method is used for high-efficiency high-yield preparation of the diaryl ester compound under mild conditions by taking a phenol compound, an iodobenzene compound and carbon monoxide as raw materials, triethylamine as alkali and pyridine palladium as a catalyst. The method provided by the invention has the advantages of less usage amount of the palladium catalyst, high catalytic activity of the palladium catalyst, stability of the palladium catalyst to air, simple operation, short reaction time and high atom economy, opens up a low-cost, green and efficient way for preparation of diaryl ester compounds, and has broad application prospects.
An alternative route for boron phenoxide preparation from arylboronic acid and its application for C[sbnd]O bond formation
Joo, Seong-Ryu,Kim, Seung-Hoi,Lim, In-Kyun
, (2020/08/06)
An efficient synthetic route to benzyl phenyl ether preparation has been successfully developed via a one-pot synthetic protocol utilizing a combination of arylboronic acids, hydrogen peroxide (H2O2), and benzyl halides. The whole procedure consists of two consecutive reactions, formation of boron phenoxide from arylboronic acids and its nucleophilic attack. A simple operation under mild conditions such as room-temperature ionic liquid (choline hydroxide), aerobic environment, and absence of metal- and base-catalysts has been employed. Expansion to utilize benzyl surrogates was also successfully accomplished.
Palladium-Catalyzed Aerobic Oxidative Coupling of Amides with Arylboronic Acids by Cooperative Catalysis
Li, Yue,Wu, Hongxiang,Zeng, Zhuo
, p. 4357 - 4361 (2019/07/09)
The first fluoride and palladium co-catalyzed conversion of amide to ester through an aerobic oxidative coupling pathway is reported. This new approach presents a practical process that employs easily available oxygen and commercially available arylboronic acids as coupling partners, uses a wide range of N- tosylamides, and proceeds under mild reaction conditions. This protocol demonstrates broad functional group tolerance, and provides an alternative option to synthesize esters from N-tosylamides which obtained by simply N-functionalization of secondary amides.
Enol Ester Intermediate Induced Metal-Free Oxidative Coupling of Carboxylic Acids and Arylboronic Acids
Xu, Xianjun,Feng, Huangdi,Li, Huiqiong,Huang, Liliang
, p. 3921 - 3928 (2019/06/24)
A facile, efficient and environmentally friendly methodology for the preparation of phenolic esters is realized via metal-free coupling of carboxylic acids and arylboronic acids. This sequential one pot reaction, employing methyl propiolate as an activating reagent, proceeds through the formation of enol ester intermediate, followed by a nucleophilic attack on the C-O bond under the oxidation of hydrogen peroxide. These studies display that enol esters, despite previously being overlooked as synthetic intermediates, would be the valuable building blocks for developing carbon–carbon and carbon–heteroatom bond-forming reactions.
Palladium Catalyzed Carbonylative Coupling for Synthesis of Arylketones and Arylesters Using Chloroform as the Carbon Monoxide Source
Sharma, Poonam,Rohilla, Sandeep,Jain, Nidhi
, p. 1105 - 1113 (2018/06/18)
We describe a modular, palladium catalyzed synthesis of aryl(hetero)aryl benzophenones and aryl benzoates from aryl(hetero)aryl halides using CHCl3 as the carbonyl source in the presence of KOH. The reaction occurs in tandem through an initial carbonylation to generate an aroyl halide, which undergoes coupling with arylboronic acids, bornonates, and phenols. Direct carbonylative coupling of indoles at the third position has also been accomplished under slightly modified reaction conditions by in situ activation of the C-H bond. Notably, CHCl3 is a convenient and safe alternation of CO gas, provides milder reaction conditions with high functional group tolerance, and gives the products in moderate to good yields.
