62594-94-9

Upstream product

• 106-44-5 p-cresol 
• 536-74-3 phenylacetylene 
• 111864-81-4 5-methyl-3-phenyl-2,3-dihydrobenzofuran 
• 6627-55-0 2-bromo-p-cresol 
• 14900-39-1 phenylvinylboronic acid 
• 86608-97-1 2-(1-hydroxy-1-phenylethyl)-4-methylphenol 
• 98-86-2 acetophenone 
• 4545-21-5 acetophenone p-toluenesulfonylhydrazone 
• 1470-57-1 2-hydroxy-5-methylbenzophenone 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 1450-72-2 5-methyl-2-hydroxyacetophenone 
• 108-86-1 bromobenzene 
• 98-88-4 benzoyl chloride 
• 614-34-6 p-cresyl benzoate 

Downstream Products

• 1817-67-0 4-methyl-2-(1-phenylethyl)phenol 
• 1817-67-0 (S)-4-methyl-2-(1-phenylethyl)phenol 
• 16299-22-2 6-methyl-4-phenylchromen-2-one 
• 124936-74-9 N,N-diiso-propyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropanamine 
• 209747-04-6 2-hydroxy-6-methyl-4-phenyldihydrobenzopyran 
• 14385-52-5 5-methyl-3-phenyl-2,3-benzofuran 
• 1470-57-1 2-hydroxy-5-methylbenzophenone 

Relevant academic research and scientific papers

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.

ORGANIC COMPOUNDS

Disclosed are TRPM8 modulators as defined by formula (I) for achieving a cooling effect on skin and mucousa.

Asymmetric Hydroesterification of Diarylmethyl Carbinols

An efficient asymmetric hydroesterfication of diarylmethyl carbinols is developed for the first time with a Pd-WingPhos catalyst, resulting in a series of chiral 4-aryl-3,4-dihydrocoumarins in excellent enantioselectivities and good yields. The method features mild reaction conditions, a broad substrate scope, use of easily accessible starting materials, and low palladium loadings. A plausible stereochemical model is also proposed with the Pd-WingPhos catalyst. This method has enabled a 4-step asymmetric synthesis of (R)-tolterodine from readily available starting materials.

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

Supported phosphotungstic acid catalyst on mesoporous carbon with bimodal pores: A superior catalyst for Friedel-Crafts alkenylation of aromatics with phenylacetylene

Supported phosphotungstic acid (PTA) catalysts on diverse carriers containing the modified commercially available activated carbon (AC), classical mesoporous carbon via SBA-15 hard template method (CMK-3), and the mesoporous carbon with high surface area and bimodal pores through evaporation-induced tri-constituent co-assembly approach (MC) by using a facile wet impregnation method were employed as solid acid catalysts for Friedel-Crafts alkenylation of p-xylene with phenylacetylene. N2 adsorption–desorption, X-ray diffraction (XRD), and NH3 temperature-programmed desorption (NH3-TPD) characterization techniques were employed to reveal the structure-performance relationship. PTA/MC exhibits much superior catalytic performance to the previously reported PTA/AC, and even to PTA/CMK-3. The PTA/MC catalysts were optimized by varying the PTA loading, and the optimum PTA loading is 35%. The close to 100% of conversion towards phenylacetylene can be achieved in the presence of 2.67% of the 35% PTA/MC solid acid catalyst. It is also found that catalytic properties of the solid acids are strongly depended on acidic properties that affected by the textural properties of supports and PTA loading, as well as the accessibility of active sites affected by specific surface area and pore structure of catalyst. Moreover, the 35?wt.% PTA/MC catalyst has demonstrated outstanding catalytic performance for the Friedel-Crafts alkenylation of diverse aromatics to their corresponding α-arylstyrenes.

Supported phosphotungstic acid catalyst on modified activated carbon for Friedel-Crafts alkenylation of diverse aromatics to their corresponding α-arylstyrenes

Abstract The supported phosphotungstic acid catalysts on modified activated carbon (PTA/AC) prepared by a facile wet impregnation method were employed for Friedel-Crafts alkenylation of diverse aromatics with phenylacetylene to synthesize their corresponding α-arylstyrenes. Reaction results demonstrate that the fabricated PTA/AC catalyst with 30 wt.% PTA loading exhibits outstanding catalytic performance. The 100% conversion of phenylacetylene with 95.7% selectivity towards α-(2,5-dimethylphenyl) styrene can be achieved over the developed 30 wt.% PTA/AC catalyst under optimized reaction conditions, and no visible loss in catalytic performance can be observed after it suffers from several times recycling. The various characterization techniques including X-ray diffraction, N2 adsorption-desorption, Fourier transform infrared spectroscopy, and NH3 temperature-programmed desorption were employed to reveal the relationship between the catalysts nature and catalytic properties. Moreover, the results on the scope of aromatics for the Friedel-Crafts alkenylation illustrate that the developed PTA/AC alkenylation catalyst can be efficiently catalyze the diverse aromatics and even for the electron deficient chlorobenzene. The developed PTA/AC catalyst, using the modified low-cost and sustainable AC as support, may be a robust and promising candidate for highly-efficient and clean α-arylstyrenes production through Friedel-Crafts alkenylation of diverse aromatics including electron-donating and electron-withdrawing groups substituted benzene derivatives as well as heterocyclic and polypolycyclic arenes with phenylacetylene.

OH-directed alkynylation of 2-vinylphenols with ethynyl benziodoxolones: A fast access to terminal 1,3-enynes

The first direct alkynylation of 2-vinylphenols was developed. The rationally optimized hypervalent iodine reagent TIPS-EBX in combination with [(CpRhCl2)2] as a C-H-activating transition metal catalyst enables the construction of a variety of highly substituted 1,3-enynes in high yields of up to 98 %. This novel C-H activation method shows excellent chemoselectivity and exclusive (Z)-stereoselectivity, and it is also remarkably mild and tolerates a variety of functional groups. Furthermore, synthetic modifications of the resulting 1,3-enynes were demonstrated. To our knowledge, this is the first example for an OH-directed C-H alkynylation with hypervalent iodine reagents.

Rhodium(III)-catalyzed ortho alkenylation of n-phenoxyacetamides with n-tosylhydrazones or diazoesters through C-H activation

A coupling reaction of N-phenoxyacetamides with N-tosylhydrazones or diazoesters through RhIII-catalyzed C-H activation is reported. In this reaction, ortho-alkenyl phenols were obtained in good yields and with excellent regio- and stereoselectivity. Rh-c

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