72209-52-0

Upstream product

• 100-42-5 styrene 
• 135-19-3 β-naphthol 
• 530-93-8 1,2,3,4-tetrahydronaphthalen-2-one 
• 98-85-1 1-Phenylethanol 
• 93-92-5 1-phenylethyl acetate 
• 33863-82-0 4-methyl-N-(1-phenylethyl)aniline 
• 72209-51-9 α-methyl-N-(2-methylphenyl)benzenemethanamine 

Relevant academic research and scientific papers

3D Nanoporous FeAl-KIT-5 with a cage type pore structure: A highly efficient and stable catalyst for hydroarylation of styrene and arylacetylenes

A novel bimetallic nanoporous FeAl-KIT-5 catalyst with a cage type porous structure and a high surface area has been prepared for the hydroarylation of styrene and arylacetylenes to afford 1,1-diarylalkanes and 1,1-diarylalkenes, respectively. The catalyst was found to be highly active, and selective, affording a high yield of substituted alkanes and alkenes. The catalyst also showed much higher activity as compared to those of other nanoporous catalysts such as AlSBA-15, AlKIT-5, and FeKIT-5, and can be reused several times without much loss of its activity.

Phosphorous acid-catalyzed alkylation of phenols with alkenes

A H3PO3-catalyzed alkylation of phenols with alkenes is achieved in a facile, efficient, and selective manner. The reaction shows a unique selectivity, i.e., excellent regioselectivity, thorough suppression of overalkylation, without alkylation of a simple phenyl ring, and can selectively provide ortho-, meta-, or para-alkylated phenol derivatives in good to excellent yields. This feature along with mild reaction conditions, sensitive functional group tolerance, and scale-up synthesis and late modification of phenolic bioactive compounds make it an ideal and practical alternative for the modification of phenols.

Preparation method of alkylphenol compounds

The invention provides a method for preparing alkylphenol compounds from phenol compounds and olefin. The method has the characteristics of cheap and easily available raw materials, simple reaction system, simplicity in reaction operation, wide substrate range, compatibility with groups such as CHO and COOH, and excellent regioselectivity, generates no overalkylation products due to only alkylation of phenol and no influence on common aryl groups, and can be used for modifying drug intermediates. The method mainly solves the problems of harsh conditions such as use of a strong Lewis catalyst,poor functional group compatibility, poor selectivity, need of prefabrication of a catalyst material and the like in other methods, and H3PO3 plays a dual role in the same system, can promote alkene to generate carbocations, and also can inhibit isomerization of phenol.

A simple Lewis acid induced reaction of phenols with electrophiles: Synthesis of functionalized 4H-chromenes and ortho-benzylphenols

Lewis acid ZnCl2 promoted cyclization protocol to 4H-chromenes is accomplished, using readily available phenols and acetophenones as starting materials. Interestingly, the process is feasible under the solvent free environment. Synthesis of a variety of 4H-chromenes have been accomplished using this strategy. In addition, this concept is extended to the synthesis of ortho-benzylphenols by treating phenols either with styrenes or secondary benzylic alcohols.

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.

Microwave assisted benzylation of naphthols and 4-hydroxycoumarin under catalyst & solvent free conditions

An expeditious and highly practical, microwave assisted benzylation of naphthols and 4-hydroxycoumarin has been developed under catalyst-free & solvent-free conditions. Alcohols undergo heat induced dehydration to form ethers, which collapse reversibly to form the carbocation which was captured immediately by a suitable nucleophile to furnish the benzylated compounds.

Catalytic Tandem and One-Pot Dehydrogenation-Alkylation and -Insertion Reactions of Saturated Hydrocarbons with Alcohols and Alkenes

The ruthenium-hydride catalyst has been successfully used for the tandem sp3 C-H dehydrogenation-alkylation reaction of saturated hydrocarbon substrates with alcohols to form the alkyl-substituted alkene and arene products. The analogous one-pot dehydrogenation-insertion of saturated ketones with alkenes and dienes directly yielded synthetically useful 2-alkylphenol and benzopyran products in a highly regio- and stereoselective manner without forming any wasteful byproducts. (Chemical Equation Presented).

Graphene-Catalyzed Direct Friedel-Crafts Alkylation Reactions: Mechanism, Selectivity, and Synthetic Utility

Transition-metal-catalyzed alkylation reactions of arenes have become a central transformation in organic synthesis. Herein, we report the first general strategy for alkylation of arenes with styrenes and alcohols catalyzed by carbon-based materials, exploiting the unique property of graphenes to produce valuable diarylalkane products in high yields and excellent regioselectivity. The protocol is characterized by a wide substrate scope and excellent functional group tolerance. Notably, this process constitutes the first general application of graphenes to promote direct C-C bond formation utilizing polar functional groups anchored on the GO surface, thus opening the door for an array of functional group alkylations using benign and readily available graphene materials. Mechanistic studies suggest that the reaction proceeds via a tandem catalysis mechanism in which both of the coupling partners are activated by interaction with the GO surface.

Hydroarylation of styrenes with electron-rich arenes over acidic ion-exchange resins

A series of acidic cation-exchange resins were used for the hydroarylation of resorcinol with styrene, in which resin D072 exhibited the excellent catalytic performance in this reaction with 99% conversion of styrene and 90% selectivity of 4-(1-phenylethyl)resorcinol. It was applied to the hydroarylation of various electron-rich arenes with styrenes, and the hydroarylated products were quantitatively obtained. This catalyst could be used for four consecutive runs with slight decrease in activity. The hydroarylation of resorcinol with styrene over resin D072 in a fixed bed was completed effectively with 94% selectivity and 99% conversion, and this green continuous process is potentially applicable to large-scale productions.

H-β-zeolite-catalysed hydroarylation of styrenes

The hydroarylation of styrenes with various arene(heteroarene) compounds using H-β-zeolite as a green and recyclable heterogeneous catalyst under mild reaction conditions has been developed. The catalyst showed versatility and high selectivity (up to 100a€‰%) of desired 1,1-diarylalkanes in cyclohexane as solvent under the conditions studied. The catalyst could be reactivated by simple treatment with mineral acid at room temperature for better catalytic activity. Hydroarylation of styrenes with variousarene(heteroarene) compounds using H-β-zeolite as a green, heterogeneous and reusable catalyst under mild conditions is reported.