25433-77-6Relevant academic research and scientific papers
Dual Photoredox/Gold Catalysis Arylative Cyclization of o-Alkynylphenols with Aryldiazonium Salts: A Flexible Synthesis of Benzofurans
Xia, Zhonghua,Khaled, Omar,Mouriès-Mansuy, Virginie,Ollivier, Cyril,Fensterbank, Louis
, p. 7182 - 7190 (2016/08/30)
A new method for the arylative cyclization of o-alkynylphenols with aryldiazonium salts via dual photoredox/gold catalysis is described. The reaction proceeds smoothly at room temperature in the absence of base and/or additives and offers an efficient app
A one-pot domino C-H, C-C activation in coumarins: A fast track to 2,3-diaryl benzo[b]furans
Khoobi, Mehdi,Molaverdi, Fatemeh,Jafarpour, Farnaz,Abbasnia, Masoumeh,Kubicki, Maciej,Shafiee, Abbas
supporting information, p. 11713 - 11716 (2015/07/15)
An approach to synthesize 2,3-diaryl benzo[b]furans using coumarins and aryl bromides is developed. This state-of-the-art strategy capitalizes on a palladium-catalyzed one-pot decarbonylative diarylation of coumarins, paving the way to achieve biologicall
Efficient microwave-assisted one-pot three-component synthesis of 2,3-disubstituted benzofurans under Sonogashira conditions
Markina, Nataliya A.,Chen, Yu,Larock, Richard C.
, p. 2701 - 2713 (2013/03/28)
An efficient one-pot method for the synthesis of 2,3-disubstituted benzo[b]furans from commercially available 2-iodophenols, terminal acetylenes and aryl iodides has been developed utilizing Sonogashira reaction conditions. After an initial Sonogashira coupling of the 2-iodophenol with the terminal alkyne, cyclization involving the aryl iodide provides the 2,3-disubstituted benzo[b]furan in good to excellent yields. The use of microwave irradiation shortens the reaction times and minimizes the side products. This methodology is especially useful for the construction of libraries of highly substituted benzo[b]furans and their analogues.
Synthesis of Conformationally Restricted 2,3-Diarylbenzo[b]furan by the Pd-Catalyzed Annulation of o-Alkynylphenols: Exploring a Combinatorial Approach
Hu, Youhong,Nawoschik, Kenneth J.,Liao, Yun,Ma, Jian,Fathi, Reza,Yang, Zhen
, p. 2235 - 2239 (2007/10/03)
The palladium/bpy-catalyzed annulation of o-alkynylphenol with various aryl halides to generate diversified 2,3-diarylbenzo[b]furan is herein described. This method provides an efficient synthetic pathway for the combinatorial synthesis of conformationally restricted 2,3-diarylbenzo[b]furan for drug discovery.
Competition of mechanisms in the photochemical cleavage of the C-X bond of aryl-substituted vinyl halides
Galli, Carlo,Gentili, Patrizia,Guarnieri, Alessandra,Kobayashi, Shinjiro,Rappoport, Zvi
, p. 9292 - 9299 (2007/10/03)
The photolysis of aryl halides caused homolysis of the carbon-halogen bond and formation of aryl radicals. In contrast, photolysis of vinyl halides can induce both heterolysis of the C-X bond, thereby generating vinyl cations, and homolysis, giving vinyl radicals. Examples of this competition among pathways is reported here for three vinylic precursors, namely, 1,2,2- triphenylbromoethene (1), 1-phenyl-2,2-bis(o-methoxyphenyl)-1-bromoethene (11), and β-bromostyrene (19). Incursion of the photoinduced S(RN)1 process, through the intermediacy of the vinyl radical, is verified in the presence of reducing nucleophiles, such as the enolate ions of ketones, and in part with (EtO)2PO-. Conversely, incursion of the heterolytic path, and intermediacy of the vinyl cation, occurs in the presence of weak electron-donor anions, such as NO2-, N3-, and Cl-. The vinyl cation produced from 19, which is less stable than those derived from 1 and 11, gives phenylacetylene via an E1-type elimination. An estimate is provided for the intramolecular rate of interception of the vinyl cation derived from 11 by the ortho-methoxy groups of the β-o-anisyl substituents. Finally, evidence against a photoinduced electron transfer from RO- ions to vinyl halide 1 is presented.
Photochemistry of Vinyl Halides. Formation of Benzofurans by Photolysis of β-(o-Methoxyphenyl)vinyl Bromides
Suzuki, Tatsuo,Kitamura, Tsugio,Sonoda, Taka-aki,Kobayashi, Shinjiro,Taniguchi, Hiroshi
, p. 5324 - 5328 (2007/10/02)
Photolysis of β,β-bis(o-methoxyphenyl)-substituted vinyl bromides gave benzofuran derivatives which are derived from an intramolecular nucleophilic attack of the methoxyl group on an intermediate vinyl cation.With α-aryl-substituted vinyl bromides, only o
