39477-86-6

Upstream product

• 58972-42-2 1-(2-hydroxyphenyl)-1-phenyl-ethanol 
• 98-86-2 acetophenone 
• 108-95-2 phenol 
• 536-74-3 phenylacetylene 
• 57049-58-8 3-phenyl-2,3-dihydrobenzofuran 
• 32250-84-3 1-(2-methoxy-phenyl)-1-phenyl-ethanol 
• 118-93-4 o-hydroxyacetophenone 
• 95-56-7 2-hydroxybromobenzene 
• 14900-39-1 phenylvinylboronic acid 
• 100-42-5 styrene 
• 5661-50-7 N-(phenoxy)acetamide 
• 4545-21-5 acetophenone p-toluenesulfonylhydrazone 
• 100-58-3 phenylmagnesium bromide 
• 108-86-1 bromobenzene 

Downstream Products

• 120346-43-2 1-(4-hydroxyphenyl)-1-phenylethane 
• 24892-80-6 2-(1-phenylvinyl)anisole 
• 99477-30-2 2-propanoic acid 
• 29909-72-6 3-Phenylbenzofuran 
• 1379805-14-7 C₁₄H₁₂O₂ 
• 1379805-13-6 3-(2-hydroxyphenyl)-3-phenylacrylic acid 
• 15185-05-4 4-phenylcoumarin 
• 117-99-7 2-Hydroxybenzophenone 
• 4355-42-4 3-methyl-3-phenylbenzofuran-2(3H)-one 
• 61198-52-5 3,4-dihydro-4-phenyl-2H-1-benzopyran-2-one 
• 1610359-50-6 1,2,4-triphenylspiro[4,5]deca-1,3,7,9-tetraen-6-one 
• 1610359-65-3 C₂₈H₁₉⁽²⁾HO 
• 13054-95-0 2,3-diphenylbenzofuran 

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.).

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.

Photocatalyzed Intramolecular [2+2] Cycloaddition of N-Alkyl-N-(2-(1-arylvinyl)aryl)cinnamamides

N-Alkyl-N-(2-(1-arylvinyl)aryl)cinnamamides are converted into natural product inspired scaffolds via iridium photocatalyzed intramolecular [2+2] photocycloaddition. The protocol has a broad substrate scope, whilst operating under mild reaction conditions. Tethering four components forming a trisubstituted cyclobutane core builds rapidly high molecular complexity. Our approach allows the design and synthesis of a variety of tetrahydrocyclobuta[c]quinolin-3(1H)-ones, in yields ranging between 20–99 %, and with excellent regio- and diastereoselectivity. Moreover, it was demonstrated that the intramolecular [2+2]-cycloaddition of 1,7-enynes—after fragmentation of the cyclobutane ring—leads to enyne-metathesis-like products.

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.

Spherical hollow mesoporous silica supported phosphotungstic acid as a promising catalyst for α-arylstyrenes synthesis via Friedel-Crafts alkenylation

In this work, a spherical hollow mesoporous silica (SHMS) with high surface area (902 m2/g) and large mesopore volume (1.31 cm3/g) was prepared via a facile and scalable two-step soft-hard dual template-assisted sol-gel approach (OSD

Practical, Large-Scale Preparation of Benzoxepines and Coumarins through Rhodium(III)-Catalyzed C-H Activation/Annulation Reactions

Herein we disclose the assembly of benzoxepines and coumarins from 2-alkenylphenol precursors using [Cp*RhCl2]2 as the precatalyst and alkynes or carbon monoxide as reacting partners. The preparation of benzoxepines and coumarins can be scaled up to 33 mmol using low catalyst loadings.

A chiral phosphorus alkene ligand, synthetic method and the application of the asymmetric reaction in (by machine translation)

The invention relates to a chiral phosphorus alkene ligand, a synthesis method and application thereof in asymmetric reaction. Specifically, the invention discloses a chiral phosphorus alkene compound, which has a structural formula shown as formula I or formula II in the specification, wherein R, R, R, R, R, R, R, R and R are defined in the specification. The chiral phosphorus alkene compound can be prepared from chiral 2, 2'-binaphthol or its derivative as the starting material through two to four steps of reaction by means of four methods. The chiral phosphorus alkene compound can be used as a chiral ligand in asymmetric addition reaction of rhodium catalyzed boric acid and prochiral C=X (X=C, O, N) double bond, and can achieve good yield and enantioselectivity.

Tuning of the textural features and acidic properties of sulfated mesoporous lanthana-zirconia solid acid catalysts for alkenylation of diverse aromatics to their corresponding α-arylstyrenes

The textural features and acidic properties of sulfated mesoporous lanthana-zirconia solid acids (SO42?/meso-La0.1Zr0.9Oδ) were efficiently tuned by modifying the conditions used to prepare the meso-La0.1Zr0.9Oδ composites, such as the molar ratio of the template to La and Zr metal ions (Nt/m), molar ratio of ammonia to La and Zr metal ions (Na/m), hydrothermal temperature (Thydro), and hydrothermal time (thydro). The effect of the textural features and acidic properties on the catalytic performance of solid acid catalysts for alkenylation of p-xylene with phenylacetylene was investigated. Various characterization techniques such as N2 physisorption, X-ray diffraction, NH3 temperature-programmed desorption, and thermogravimetric analysis were employed to reveal the relationship between the nature of catalyst and its catalytic performance. It was found that the catalytic performance significantly depended on the textural features and acidic properties, which were strongly affected by preparation conditions of the meso-La0.1Zr0.9Oδ composite. Appropriate acidic sites and high accessibility were required to obtain satisfactory catalytic reactions for this reaction. It was also found that the average crystallite size of t-ZrO2 affected by the preparation conditions had significant influence on the ultrastrong acidic sites of the catalysts. The optimized SO42?/meso-La0.1Zr0.9Oδ catalyst exhibited much superior catalytic activity and coke-resistant stability. Moreover, the developed SO42?/meso-La0.1Zr0.9Oδ catalyst demonstrated excellent catalytic performance for alkenylation of diverse aromatics with phenylacetylene to their corresponding α-arylstyrenes. Combining the previously established complete regeneration of used catalysts by a facile calcination process with the improved catalytic properties, the developed SO42?/meso-La0.1Zr0.9Oδ solid acid could be a potential catalyst for industrial production of α-arylstyrenes through clean and atom efficient solid-acid-mediated Friedel-Crafts alkenylation of diverse aromatics with phenylacetylene.

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.