35307-35-8Relevant academic research and scientific papers
Indium(III)-Catalyzed Synthesis of Benzo[ b]furans by Intramolecular Hydroalkoxylation of ortho-Alkynylphenols: Scope and Mechanistic Insights
Alonso-Mara?ón, Lorena,Martínez, M. Montserrat,Sarandeses, Luis A.,Gómez-Bengoa, Enrique,Pérez Sestelo, José
, p. 7970 - 7980 (2018/06/22)
Indium(III) halides catalyze the hydroalkoxylation reaction of ortho-alkynylphenols to afford benzo[b]furans in good yields. The reaction proceeds with 5-endo-dig regioselectivity with a variety of phenols functionalized at the arene and alkyne moieties in high yields using InI3 (5 mol %) in DCE. Experimental and computational studies support a mechanism based on the indium(III) π-Lewis acid activation of the alkyne followed by nucleophilic addition of the phenol and final protodemetalation to afford the corresponding benzo[b]furan. DFT calculations suggest that dimer In2I6 is the catalytic species through a novel double coordination with the alkyne and the hydroxyl group.
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
One-pot synthesis of 2,3-diarylbenzofurans via sequential iodocyclization and Pd-catalyzed Suzuki coupling reactions of 2-alkynylanisoles with boronic acids in water
Han, Jiang-Sheng,Chen, Su-Qin,Zhong, Ping,Zhang, Xiao-Hong
, p. 3148 - 3155 (2015/10/06)
An efficient approach for the one-pot synthesis of 2,3-diarylbenzofurans via sequential iodocyclization and Pd-catalyzed Suzuki coupling reaction of 2-alkynylanisoles with boronic acids in water is reported. The protocol utilizes water as the solvent and
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.
Cyclodeshydratation d'aryloxy-2 diaryl-1,2 ethanones en diaryl-2,3 benzofurannes. Influence de la substitution sur la competition entre deux chemins reactionnels
Montfort, Bernard,Laude, Bernard,Vebrel, Joel,Cerutti, Ernest
, p. 848 - 854 (2007/10/02)
Many of the methods for synthesizing derivatives of 2,3-diaryl benzofurans imply cyclodehydration of 1,2-diaryl 2-aryloxyethanones, leading often to a mixture of two isomers which differ by the presence of the aryl substituent at positions C-2 or C-3 of benzofuran.This isomerisation is explained by a competition between two possible mechanisms.Either a direct electrophilic substitution or the intermediate formation of an α-acylcarbenium ion.This study deals with the competition as determined by the substitution of aryl groups in the initial substrate.Each 2,3-diarylbenzofuran was synthesized previously using an unambiguous method.
