62594-99-4Relevant academic research and scientific papers
B(C6F5)3-Catalyzed Hydroarylation of Aryl Alkynes for the Synthesis of 1,1-Diaryl and Triaryl Substituted Alkenes
Chen, Hui,Gao, Liuzhou,Liu, Xueting,Wang, Guoqiang,Li, Shuhua
supporting information, p. 5238 - 5242 (2021/10/19)
A new strategy for the synthesis of 1,1-diaryl and triarylsubstituted alkenes has been developed utilizing B(C6F5)3-catalyzed hydroarylation of alkynes with phenols. The method provides a direct route to ortho-alkenylated phenols with both terminal and internal alkynes. The reactions show excellent regioselectivity, and good stereoselectivity was observed for the hydroarylation of internal alkynes. Computational and experimental studies suggest that for the reaction of internal alkynes and phenols, an acid-catalyzed isomerization mechanism involving two tertiary carbonium ion intermediates is responsible for the formation of Z-triaryl substituted alkenes.
B(C6F5)3-Catalyzed Hydroarylation of Terminal Alkynes with Phenols
Huang, Jin,Huang, Liangbin,Jiang, Huanfeng,Lu, Changhui,Zhou, Jiaming
supporting information, p. 3962 - 3967 (2021/07/26)
We developed a B(C6F5)3 catalyzed hydroarylation of terminal alkynes with various phenols at room temperature without adding any additives, leading to the synthesis of 2-gem-vinylphenols with good regio-selectivity. Those transformations featured a broad substrate scope with moderate yields. Mechanism studies indicated that those transformations proceeded through the activation of phenol by B(C6F5)3 with subsequent protonation of alkyne/Friedel-Crafts-type reaction. (Figure presented.).
A Bifunctional Ligand Enables Gold-Catalyzed Hydroarylation of Terminal Alkynes under Soft Reaction Conditions
Cheng, Xinpeng,Kong, Weiguang,Li, Bo,Li, Ting,Luo, Baomin,Yang, Hao,Yang, Yuhan,Zhang, Liming,Zong, Luyi
supporting information, (2020/07/30)
An efficient gold-catalyzed hydroarylation of alkynes under soft reaction conditions is developed by utilizing a bifunctional ligand. This transformation features a broad substrate scope and thus exhibits moderate to excellent efficiency.
Method for preparing disubstituted olefin through hydroarylation of terminal alkyne
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Paragraph 0021-0023, (2020/09/16)
The invention discloses a method for preparing disubstituted olefin through hydroarylation of terminal alkyne. The method comprises the following steps: mixing terminal alkyne, 2-naphthol, a catalystL1AuCl, NaBARF and a solvent in a reaction bottle, carry
Hydroarylation of alkynes and alkenes through alumina-sulfuric acid catalyzed regioselective C–C bond formation
Pramanik, Amit,Ghatak, Avishek,Khan, Sagar,Bhar, Sanjay
supporting information, p. 1091 - 1095 (2019/03/26)
A highly atom-efficient synthetic protocol for hydroarylation of terminal-aryl alkynes and styrene through the regioselective C–C bond formation via the electrophilic addition of naphthols and substituted phenols has been developed using alumina-sulfuric acid as a heterogeneous supported solid acid catalyst. This methodology shows excellent regioselectivity and affords the desired product in good to excellent yield. The heterogeneous catalyst can also be recycled efficiently without much loss of activity.
Ruthenium(II)-Catalyzed Dearomatized C?H Activation and Annulation Reaction of Vinylnaphthols with Alkynes: Access to Spiro-Pentacyclic Naphthalenones
Duarah, Gauri,Kaishap, Partha P.,Sarma, Bipul,Gogoi, Sanjib
supporting information, p. 10196 - 10200 (2018/07/29)
The ruthenium(II)-catalyzed annulation of vinylnaphthols and alkynes is described. The reaction proceeds through C?H activation, dearomatization, and alkyne insertion. This reaction affords spiro-pentacyclic naphthalenones that have biological significance in good yields.
Iodine-Mediated, Microwave-Assisted Synthesis of 1-Arylnaphthofurans via Cyclization of 1-(1′-Arylvinyl)-2-naphthols
Rao, V. Kameshwara,Kaswan, Pinku,Shelke, Ganesh M.,Ryan, Ashley,Jha, Mukund,Kumar, Anil
, p. 3990 - 3996 (2015/12/18)
A metal-free, one-pot, iodine-mediated, microwave-assisted cyclization of 1-(1′-arylvinyl)-2-naphthols (ortho-vinylnaphthols) into 1-arylnaphthofurans is developed. The 1-arylnaphthofurans are isolated in good to excellent yields (65-90%) using two equiva
Hydroarylation of Alkynes with Phenols in the Presence of Gallium Complexes of a Labile N-Ligand: Synthesis of Chromenes
Moskalev, Mikhail V.,Yakub, Arkadiy M.,Morozov, Alexander G.,Baranov, Evgenii V.,Kazarina, Olga V.,Fedushkin, Igor L.
, p. 5781 - 5788 (2015/09/15)
In the presence of (dpp-bian)Ga-Ga(dpp-bian) (1) and [dpp-bian(Ph)C=C(H)]Ga-Ga[(H)C=C(Ph)dpp-bian] (2) {dpp-bian = 1,2-bis[(2,6-diisopropylphenyl)imino]acenaphthene}, phenylacetylene reacts with 1-naphthol to give 2-(1-phenylvinyl)naphthalen-1-ol (3). In
A simple and efficient synthesis of 2,3-diarylnaphthofurans using sequential hydroarylation/Heck oxyarylation
Rao, V. Kameshwara,Shelke, Ganesh M.,Tiwari, Rakesh,Parang, Keykavous,Kumar, Anil
supporting information, p. 2190 - 2193 (2013/06/05)
An efficient and simple strategy has been developed for the synthesis of 2,3-diarylnaphthofurans using sequential hydroarylation of naphthols and alkynes in the presence of In(OTf)3 under microwave irradiation followed by one-pot Heck-oxyarylat
Benzofurans from benzophenones and dimethylacetamide: Copper-promoted cascade formation of furan O1-C2 and C2-C3 bonds under oxidative conditions
Moure, Maria J.,Sanmartin, Raul,Dominguez, Esther
supporting information; experimental part, p. 3220 - 3224 (2012/05/05)
DMA donates: Copper(II) acetate and 8-hydroxyquinoline promote the formation of a benzofuran core through a cascade of copper-catalyzed processes wherein the key carbon atom comes from the dimethylacetamide (DMA) solvent. Strong evidence for the participation of a Wacker cyclization catalyzed solely by copper is provided, not only in the title reaction from benzophenones but also from 2-hydroxy-α-arylstyrene derivatives. Copyright
