62594-98-3

Upstream product

• 150-76-5 4-methoxy-phenol 
• 536-74-3 phenylacetylene 
• 17332-11-5 2-bromo-4-methoxyphenol 
• 4545-21-5 acetophenone p-toluenesulfonylhydrazone 
• 98-86-2 acetophenone 
• 86608-98-2 5-methoxy-2-hydroxy-α-methyl-α-phenyl-benzene-methanol 
• 14900-39-1 phenylvinylboronic acid 

Downstream Products

• 1275593-42-4 (S)-4-methoxy-2-(1-phenylethyl)phenol 
• 7196-05-6 5-methoxy-3-phenylbenzofuran 
• 40547-03-3 6-Methoxy-4-phenyl-2H-1-benzopyran-2-one 
• 14770-95-7 2,3-diphenyl-5-methoxybenzofuran 

Relevant academic research and scientific papers

B(C6F5)3-Catalyzed Hydroarylation of Terminal Alkynes with Phenols

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.).

B(C6F5)3-Catalyzed Hydroarylation of Aryl Alkynes for the Synthesis of 1,1-Diaryl and Triaryl Substituted Alkenes

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 Sequential Additions of Terminal Alkynes to para-Substituted Phenols: Selective Construction of Congested Phenol-Substituted Quaternary Carbons

We have developed a borane-catalyzed sequential addition of terminal alkynes to para-substituted phenols, which affords a wide range of ortho-propargylic alkylated phenols bearing congested quaternary carbons. Control experiments combined with DFT calcula

Sequential One-Pot Synthesis of 3-Arylbenzofurans from N-Tosylhydrazones and Bromophenol Derivatives

A divergent and efficient one-pot sequence allowing direct access to 3-arylbenzofuran derivatives has been developed. The process, involving N-tosylhydrazones and bromophenols, proceeds via a palladium-catalyzed Barluenga-Valdés cross-coupling, followed by an aerobic, copper-catalyzed, radical cyclization to form Csp2-Csp2 and O-Csp2 bonds. 3-Arylated benzofurans bearing various substituents were obtained with good to excellent yields (up to 90%). Mechanistic investigation strongly supports a radical process for the cyclization step.

Hydroarylation of alkynes and alkenes through alumina-sulfuric acid catalyzed regioselective C–C bond formation

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.

Catalytic Availabilities of Lewis Acidic SnCl2: Ph3PAuCl–SnCl2Composite Catalyzed Successive ortho-Alkenylation/O-Alkenylation of Phenols Followed by Cyclization to 1-Benzopyrans

A Ph3PAuCl–SnCl2composite, prepared in situ from Ph3PAuCl and SnCl2, catalyzed the formation of 1-benzopyrans from phenols and phenylacetylene. The Ph3PAuCl–SnCl2composite catalyzed reactio

Iodine-Mediated, Microwave-Assisted Synthesis of 1-Arylnaphthofurans via Cyclization of 1-(1′-Arylvinyl)-2-naphthols

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

Indium triflate catalyzed microwave-assisted alkenylation of methoxyphenols: Synthesis of indenes and chromenes

In(OTf)3 catalyzed microwave-assisted alkenylation of methoxyphenols was investigated. Exclusive formation of either indenes or chromenes was observed depending on the position of the methoxy group on phenol. The structures of 1H-inden-4-ol der

Iron-containing mesoporous aluminosilicate catalyzed direct alkenylation of phenols: Facile synthesis of 1,1-diarylalkenes

The addition of phenols to aryl-substituted alkynes to form 1,1-diarylalkenes was carried out by using the Fe-Al-MCM-41 catalyst. The catalyst showed remarkable improvement in time and yield in comparison to other solid catalysts. The heterogeneous cataly

A simple and efficient synthesis of 2,3-diarylnaphthofurans using sequential hydroarylation/Heck oxyarylation

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