13130-19-3Relevant academic research and scientific papers
Copper-catalysed benzofuran synthesis: developing aryl bromide-alkenyl triflates as general heterocycle precursors
Tadd, Andrew C.,Fielding, Mark R.,Willis, Michael C.
, p. 7578 - 7581 (2007)
A range of conjugated aryl bromide-alkenyl triflates, previously described as indole precursors, are efficiently converted to the corresponding benzofurans when treated with CuI/TMEDA and potassium hydroxide.
Efficient [3,3]-sigmatropic rearrangement accelerated by a trifluoroacetyl group: Synthesis of benzofurans under mild conditions
Miyata, Okiko,Takeda, Norihiko,Morikami, Yoshiaki,Naito, Takeaki
, p. 254 - 256 (2003)
The [3,3]-sigmatropic rearrangement took place smoothly during the course of trifluoroacetylation of O-phenyl-oxime at below room temperature to give the dihydrobenzofuran or benzofuran as a result of concomitant cyclization.
Supported Pt-Ni bimetallic nanoparticles catalyzed hydrodeoxygenation of dibenzofuran with high selectivity to bicyclohexane
Cai, Chun,Wu, Pengyu
supporting information, (2021/07/10)
Catalytic hydrodeoxygenation (HDO) is one of the most effective methods to upgrade the oxygen-containing compounds derived from coal tar to valuable hydrocarbons. Herein, an efficient bimetallic catalyst Pt1Ni4/MgO was prepared and applied in the HDO of dibenzofuran (DBF). High yield (95%) of the desired product bicyclohexane (BCH) was achieved at 240 °C and 1.2 MPa of H2. Superior catalytic performance could be ascribed to the “relay catalysis” of Pt sites and Ni sites, and the reaction pathway is proposed as well. Scale-up experiment and recyclability test were also performed, which demonstrated the recyclability and promising potential application of Pt1Ni4/MgO.
Synthesis of benzofurans from the cyclodehydration of α-phenoxy ketones mediated by Eaton’s reagent
Ma, Lin,Ma, Zhanwei,Zhang, Min,Zhou, Min
, p. 426 - 436 (2020/03/23)
Cyclodehydration of α-phenoxy ketones promoted by Eaton’s reagent (phosphorus pentoxide–methanesulfonic acid) is used to prepare 3-substituted or 2,3-disubstituted benzofurans with moderate to excellent yields under mild conditions. The method provides a facile access to benzofurans from readily available starting materials such as phenols and α-bromo ketones. The reaction is highly efficient, which is attributed to the good reactivity and fluidity of Eaton’s reagent. The reaction can be applied to prepare naphthofurans, furanocoumarins, benzothiophenes, and benzopyrans.
Direct C-H α-Arylation of Enones with ArI(O2CR)2 Reagents
Sousa E Silva, Felipe Cesar,Van, Nguyen T.,Wengryniuk, Sarah E.
, p. 64 - 69 (2020/01/22)
α-Arylation of α,β-unsaturated ketones constitutes a powerful synthetic transformation. It is most commonly achieved via cross-coupling of α-haloenones, but this stepwise strategy requires prefunctionalized substrates and expensive catalysts. Direct enone C-H α-arylation would offer an atom- and step-economical alternative, but such reports are scarce. Herein we report the metal-free direct C-H arylation of enones mediated by hypervalent iodine reagents. The reaction proceeds via a reductive iodonium Claisen rearrangement of in situ-generated β-pyridinium silyl enol ethers. The aryl groups are derived from ArI(O2CCF3)2 reagents, which are readily accessed from the parent iodoarenes. The reaction is tolerant of a wide range of substitution patterns, and the incorporated arenes maintain the valuable iodine functional handle. Mechanistic investigations implicate arylation via an umpoled "enolonium" species and show that the presence of a β-pyridinium moiety is critical for the desired C-C bond formation.
Method for synthesizing benzofuran derivative by taking alpha-phenoxy-ketone as raw material
-
Paragraph 0041; 0042; 0043; 0044, (2019/04/26)
The invention discloses a method for synthesizing a benzofuran derivative by taking alpha-phenoxy-ketone as a raw material. Under shielding of inert gas, the alpha-phenoxy-ketone is dissolved in dry dichloromethane, then a mixed solution of TiCl4 and dichloromethane is dropwise added slowly, and after the indoor temperature reaction, the benzofuran derivative after separation and purification is obtained. The method for synthesizing the benzofuran derivative has the advantages that raw materials are easy to obtain, the cost is low, and reaction conditions are mild; operation is simple and easyto control, there are fewer side reactions, and the after-processing is simple; the yield of the derivative is higher, the production cost is greatly reduced, better economic benefits are achieved, and the method is suitable for industrial production.
Titanium tetrachloride promoted cyclodehydration of aryloxyketones: Facile synthesis of benzofurans and naphthofurans with high regioselectivity
Zhang, Qiu,Luo, Juan,Wang, Bingqiao,Xiao, Xiaoqin,Gan, Zongjie,Tang, Qiang
supporting information, p. 1337 - 1340 (2019/04/16)
An efficient and facile method for the synthesis of a broad series of benzofurans and naphthofurans is described. The direct intramolecular cyclodehydration of aryloxyketones in the presence of titanium tetrachloride affords the corresponding benzofurans and naphthofurans with good regioselectivity and yields.
In order to phenol and α - halo as raw material synthetic benzofuran derivatives (by machine translation)
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Paragraph 0028; 0029; 0030; 0031, (2019/04/14)
The present invention to provide a phenol and α - halo as raw materials, the role of titanium tetrachloride in the reaction of the next step high-efficient method for preparing benzofuran derivative, namely under protection of inert gas, adding phenol to and [...], then heating and stirring to reflux then adding titanium tetrachloride, finally dropping into the α - halo and [...] mixed solution, after the reaction is completed after the separation and purification to obtain the benzofuran derivatives. The synthesizing method of the invention, raw materials are easy, low cost, mild reaction conditions, the operation is simple and easy to control, less side reaction, after treatment is simple, and the product yield is high, production cost is greatly reduced, with better economic benefits, is suitable for the industrial large-scale production. (by machine translation)
One-step regioselective synthesis of benzofurans from phenols and α-Haloketones
Wang, Bingqiao,Zhang, Qiu,Luo, Juan,Gan, Zongjie,Jiang, Wengao,Tang, Qiang
, (2019/06/21)
Reported here is the direct synthesis of naphthofurans and benzofurans from readily available phenols and α-haloketones promoted by titanium tetrachloride which combines Friedel-Crafts-like alkylation and intramolecular cyclodehydration into one step. This simple protocol allows for the formation of a variety of high value naphthofurans and benzofurans within which a series of cyclic and acyclic groups are readily incorporated. This process demonstrates the advantages of high levels of regioselectivity, broad substrate scope, and moderate to excellent yields.
Rearrangements of Cycloalkenyl Aryl Ethers
T?rincsi, Mercedesz,Nagy, Melinda,Bihari, Tamás,Stirling, András,Kolonits, Pál,Novak, Lajos
, (2016/05/24)
Rearrangement reactions of cycloalkenyl phenol and naphthyl ethers and the acid-catalyzed cyclization of the resulting product were investigated. Claisen rearrangement afforded 2-substituted phenol and naphthol derivatives. Combined Claisen and Cope rearrangement resulted in the formation of 4-substituted phenol and naphthol derivatives. In the case of cycloocthylphenyl ether the consecutive Claisen and Cope rearrangements were followed by an alkyl migration. The mechanism of this novel rearrangement reaction is also discussed.
