17113-31-4Relevant academic research and scientific papers
Efficient procedure for the preparation of 2-bromofuran and its application in the synthesis of 2-arylfurans
Raheem, Mohammed-Abdul,Nagireddy, Jaipal R.,Durham, Robin,Tam, William
, p. 2138 - 2146 (2010)
A simple, straightforward, and scalable procedure for the preparation of 2-bromofuran using N-bromosuccinimide (NBS) in dimethylformamide (DMF) is reported. The described preparation is conducted on a 20 to 50g scale and does not require extractive workup procedures or chromatographic purifications. To illustrate the synthetic applications of 2-bromofuran, palladium-catalyzed Suzuki coupling reactions of the prepared 2-bromofuran with various aryl boronic acids were investigated, and moderate to good yields of 2-arylfurans were obtained. Copyright Taylor & Francis Group, LLC.
Cross-Coupling Reactions for the Preparation of 2-Arylfurans, 2-Benzylfuran and 2-Cinnamylfuran
Pelter, Andrew,Rowlands, Martin,Clements, Gillian
, p. 51 - 53 (1987)
Pd catalysed coupling between organyl bromides and either 2-lithofuran or 2-furylzinc chloride are described.Arylation by a wide variety of aromatic bromides can be carried out in high yields and on a large scale.Benzylation and cinnamylation are also
Synthesis method of monosubstituted or disubstituted furan derivatives
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Paragraph 0039-0041, (2021/09/29)
The invention relates to the field of medicine synthesis, and provides a synthesis method of monosubstituted or disubstituted furan derivatives, wherein the synthesis method can be used for synthesizing various furan derivatives with different substituent groups and has high flexibility. According to the synthesis method of the monosubstituted or disubstituted furan derivatives, 5-hydroxymethyl-[delta]2-isoxazoline derivative is used as a raw material in an acidic solvent, and the monosubstituted or disubstituted furan derivatives are synthesized in one step under the action of a metal reducing agent; and according to the method, the furan derivatives with different substituent groups can be synthesized by adopting the 5-hydroxymethyl-[delta]2-isoxazoline derivatives with different substituent groups, high flexibility is achieved, the technical scheme is simple in step and mild in reaction condition, synthesis of the furan derivatives can be achieved through a one-pot method, the reaction yield is high, and large-scale production is facilitated.
Pd Nanoparticles Embedded Into MOF-808: Synthesis, Structural Characteristics, and Catalyst Properties for the Suzuki–Miyaura Coupling Reaction
Li, Tang,Pang, Wan,Wang, Jie,Zhang, Xiaoli,Zhao, Zesheng
, (2021/07/31)
Abstract: A heterogeneous single-site catalyst Pd@MOF-808 was successfully synthesized by water-based, green synthesis procedure. The catalytic experiments exhibited the Pd@MOF-808 promoted efficiently the Suzuki–Miyaura coupling reaction without the assistance of organic phosphine ligands at atmospheric pressure conditions. The catalyst also could be applied in the gram-scale synthesis of industrially anti-inflanmatory analgestic Fenbufen. Graphic Abstract: [Figure not available: see fulltext.]
Pd-NHCs Enabled Suzuki-Miyaura Cross-Coupling of Arylhydrazines via C–N Bond Cleavage
Zeng, Xiao-Xiao,Li, Dong-Hui,Zhou, Zhen,Xu, Chang,Liu, Feng-Shou
supporting information, (2021/03/01)
We describe a highly efficient protocol for cross-coupling of phenylhydrazines with arylboronic acids by Pd-NHCs under aerobic reaction condition. A series of well-defined Pd-NHCs complexes were evaluated and the relationship between the structure and the catalytic properties was investigated. It was disclosed that the Pd-PEPPSI-IPr proved to be the robust precatalyst, providing access to a range of (hetero)biaryls in good to excellent yields.
New Nickel-Based Catalytic System with Pincer Pyrrole-Functionalized N-Heterocyclic Carbene as Ligand for Suzuki-Miyaura Cross-Coupling Reactions
Guo, Zhifo,Lei, Xiangyang
supporting information, (2021/09/11)
A new catalytic system with Ni(NO3)2·6H2O as the catalyst and a pincer pyrrole-functionalized N-heterocyclic carbene as the ligand was employed in the Suzuki-Miyaura cross-coupling reactions of aryl iodides with arylboronic acids. With 5 mol% catalyst, the catalytic reactions proceeded at 160 °C, giving coupling products in isolated yields of up to 94% in short reaction times (1-4 h). The system worked efficiently with aryl iodides bearing electron-donating or electron-withdrawing groups and arylboronic acids with electron-donating groups. Steric effects were observed for both aryl iodides and arylboronic acids. It is proposed that the reactions underwent a Ni(I)/Ni(III) catalytic cycle.
Fabrication of Graphitic Carbon Nitride-Based Film: An Emerged Highly Efficient Catalyst for Direct C—H Arylation under Solar Light
Chaubey, Surabhi,Yadav, Rajesh K.,Kim, Tae Wu,Yadav, Tara Chand,Kumar, Abhishek,Dwivedi,Pandey,Singh, Atul P.
, p. 633 - 639 (2021/02/12)
Photoredox C—H bond formation can proceed in aerobic environment under solar light and has therefore become attractive. Nowadays, different types of expensive novel metal complexes and nanomaterials have been urbanized as photocatalysts for direct C—H bon
Pyrazole-Mediated C-H Functionalization of Arene and Heteroarenes for Aryl-(Hetero)aryl Cross-Coupling Reactions
Kundu, Abhishek,Dey, Dhananjay,Pal, Subhankar,Adhikari, Debashis
, p. 15665 - 15673 (2021/11/16)
Herein we introduce a transition-metal-free protocol that involves a commercially available, inexpensive pyrazole molecule to conduct C-C cross-coupling reactions at room temperature via a radical pathway. Using this method, an aryldiazonium salt has been coupled to a wide range of arenes and heteroarenes including benzene, mesitylene, thiophene, furan, benzoxazole to result the corresponding biaryl products. The full reaction mechanism is elucidated along with the crystallographic probation of an active initiator species. A potassium-stabilized deprotonated pyrazole steers single-electron transfer to the substrate and behaves as an initiator for the reaction.
Black phosphorus as a metal-free, visible-light-active heterogeneous photoredox catalyst for the direct C-H arylation of heteroarenes
Kalay, Erbay,Kü?ükke?eci, Hüseyin,Kilic, Haydar,Metin, ?nder
supporting information, p. 5901 - 5904 (2020/06/04)
Black phosphorus (BP) is for the first time employed as a metal-free, heterogeneous photoredox catalyst for the direct C-H arylation of heteroarenes with aryl diazonium salts. The arylated heteroarenes are obtained in moderate to good yields under visible-light illumination, and the protocol is shown to be applicable for the scale-up synthesis.
Carbazole based Electron Donor Acceptor (EDA) catalysis for the synthesis of biaryl and aryl-heteroaryl compounds
Annes, Sesuraj Babiola,Ramesh, Subburethinam,Saravanan, Subramanian,Saritha, Rajendhiran
supporting information, p. 2510 - 2515 (2020/04/15)
A highly regioselective, carbazole based Electron Donor Acceptor (EDA) catalyzed synthesis of biaryl and aryl-heteroaryl compounds is described. Various indole and carbazole derivatives were screened for the Homolytic Aromatic Substitution (HAS) reaction. Tetrahydrocarbazole (THC) was very efficient for the HAS transformation and proceeded via a complex formation between diazonium salt and electron rich tetrahydrocarbazole. The UV-Vis spectroscopy technique has been used to confirm the complex formation. The in situ generated EDA complex even in a catalytic amount is found to be efficient for the Single Electron Transfer (SET) process without any photoactivation. Biaryl compounds, 2-phenylfuran, 2-phenylthiophene, and 2-phenylpyrrole and bioactive compounds such as dantrolene and canagliflozin have been synthesized in moderate to excellent yields.
