5848-60-2

Usage

Uses

Used in Organic Synthesis:
Benzene, [[(2E)-3-phenyl-2-propenyl]thio]is utilized as a starting material and intermediate in organic synthesis for the production of a range of organic chemicals. Its unique structure allows for further chemical reactions and modifications, making it a valuable component in creating complex organic molecules.
Used in Pharmaceutical Production:
Benzene, [[(2E)-3-phenyl-2-propenyl]thio]also plays a role in the production of pharmaceuticals, where its properties can be harnessed to develop new drugs or improve the synthesis of existing ones. Its presence in the synthesis process can contribute to the development of medications with specific therapeutic effects.
Used in Chemical Research:
In the field of chemical research, Benzene, [[(2E)-3-phenyl-2-propenyl]thio]is employed to study the properties and reactions of thioether functional groups and benzene rings. This can lead to a better understanding of chemical behavior and the development of new synthetic methods or applications.
It is important to handle Benzene, [[(2E)-3-phenyl-2-propenyl]thio]with care, as benzene derivatives can be toxic and potentially harmful if not managed properly. Proper safety measures should be taken to minimize risks during its use in various applications.

Upstream product

• 102680-02-4 (E)-1-phenyl-3-phenylsulfinylprop-1-ene 
• 108-98-5 thiophenol 
• 4392-24-9 Cinnamyl bromide 
• 62252-43-1 2-(3-Phenyl-2-propenyl)-oxy-3,5-dinitropyridin 
• 13702-03-9 phenyl (3-phenylprop-2-yn-1-yl) sulfide 
• 882-33-7 diphenyldisulfane 
• 5219-61-4 (phenylthio)acetonitrile 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 444575-79-5 carbonic acid 1,1-dimethylethyl 1-phenyl-2-propenyl ester 
• 930-69-8 sodium thiophenolate 
• 87802-71-9 (E)-methyl cinnamyl carbonate 
• 104-54-1 3-Phenylpropenol 
• 591-50-4 iodobenzene 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 

Downstream Products

• 112157-73-0 2-((E)-3-Phenyl-allyloxy)-cyclopent-1-enecarboxylic acid ethyl ester 
• 102680-02-4 (E)-1-phenyl-3-phenylsulfinylprop-1-ene 
• 1150634-44-8 ethyl 2-phenyl-2-(phenylthio)-3-phenyl-4-pentenoate 
• 20605-46-3 3-(benzenesulfonyl)propenylbenzene 
• 1384704-27-1 C₁₉H₂₈O 

Relevant academic research and scientific papers

Gold-catalyzed thioetherification of allyl, benzyl, and propargyl phosphates

Gold-catalyzed thioetherification of C(sp3)-O bonds is described. The reaction of allyl phosphates and thiosilanes in the presence of gold nanoparticles supported on ZrO2 proceeded efficiently under mild reaction conditions to give the corresponding allyl sulfides in excellent yields. ZrO2-Supported gold nanoparticles showed excellent catalytic turnover and reusability. In addition, the C-O bonds of benzyl and propargyl phosphates underwent thioetherification to afford benzyl and propargyl sulfides. The reaction of an optically active benzyl phosphate proceeded with excellent chirality transfer to give a benzyl sulfide with high enantiomeric purity. Control experiments corroborated that soluble gold species were responsible for the efficient thioetherification of C-O bonds of phosphates, and characterization of the catalysts revealed that cationic gold species at the surface of gold nanoparticles supported on ZrO2 served as a source for highly active catalytic species.

Hemin Catalyzed Dealkylative Intercepted [2, 3]-Sigmatropic Rearrangement Reactions of Sulfonium Ylides with 2, 2, 2-Trifluorodiazoethane

A dealkylative intercepted [2, 3]-sigmatropic rearrangement reaction of allylic sulfides with 2, 2, 2-trifluorodiazoethane (CF3CHN2) is reported, the commercially available and biocompatible catalyst hemin was found to efficiently catalyze this transformation across a diverse set of allylic sulfides with in situ generated CF3CHN2, providing excellent yields (up to 99%) under mild condition without inert gas protection. In addition, CF3CHN2 exhibited unique reactivity toward this process compared with other frequently used diazo reagents. This work expands the range of carbene-mediated transformations catalyzed by hemin and introduces a concise and general strategy for exploiting new possibility of reactions concerning organosulfides. (Figure presented.).

E-Selective Hydrothiolation of Terminal Arylallenes with Arylthiols Catalyzed by Ni (PMe3)4

A catalytic system of regioselective synthesis of allyl sulfides via hydrothiolation of terminal arylallenes with arylthiols has been developed using nickel(0) complex Ni (PMe3)4 as a catalyst. In most cases the excellent to moderate

Nanolayered cobalt-molybdenum sulphides (Co-Mo-S) catalyse borrowing hydrogen C-S bond formation reactions of thiols or H2S with alcohols

Nanolayered cobalt-molybdenum sulphide (Co-Mo-S) materials have been established as excellent catalysts for C-S bond construction. These catalysts allow for the preparation of a broad range of thioethers in good to excellent yields from structurally diverse thiols and readily available primary as well as secondary alcohols. Chemoselectivity in the presence of sensitive groups such as double bonds, nitriles, carboxylic esters and halogens has been demonstrated. It is also shown that the reaction takes place through a hydrogen-autotransfer (borrowing hydrogen) mechanism that involves Co-Mo-S-mediated dehydrogenation and hydrogenation reactions. A novel catalytic protocol based on the thioetherification of alcohols with hydrogen sulphide (H2S) to furnish symmetrical thioethers has also been developed using these earth-abundant metal-based sulphide catalysts.

Eosin-Y-Catalyzed Photoredox C?S Bond Formation: Easy Access to Thioethers

An operationally simple Eosin Y catalyzed sulfenylation of hydrazones has been realized to afford a range of thioethers under visible light. The methodology provides high yields of thioethers under ambient conditions employing readily available and inexpensive starting materials. The reaction has broad substrate scope and is compatible with various functional groups.

Palladium- and Nickel-Catalyzed Decarbonylative C-S Coupling to Convert Thioesters to Thioethers

This Letter describes the development of a catalytic decarbonylative C-S coupling reaction that transforms thioesters into thioethers. Both Pd- and Ni-based catalysts are developed and applied to the construction of diaryl, aryl alkyl, and heterocycle-containing thioethers.

Aqueous hemin catalyzed sulfonium ylide formation and subsequent [2,3]-sigmatropic rearrangements

A mild hemin catalytic system for sulfonium ylide generation via a metal carbenoid and a subsequent [2,3]-sigmatropic rearrangement reaction in aqueous solvent is well-established, with the assistance of cyclodextrin (CD) and Triton X-100. The protocol displays high catalytic activity with a broad substrate scope of aryl/alkyl allyl sulfides and diazo reagents, affording homoallyl sulfide products in up to 99% yield. Notably, this catalytic system is successful for water-insoluble allyl sulfides but ineffective for allyl amines or allyl ethers. Moreover, an unprecedented cascade reaction of sulfonium ylide formation, [2,3]-sigmatropic rearrangement and C-H insertion was reported.

One-Pot Copper-Catalysed Thioetherification of Aryl Halides Using Alcohols and Lawesson's Reagent in Diglyme

A new protocol for the thioetherification of structurally varied alcohols with aryl halides using Lawesson's reagent, catalysed by copper(I) iodide, and using diglyme as a safe solvent was developed. Using this method, the reactions of aryl halides proceeded efficiently, and the desired sulfides were obtained in high to excellent yields. The method uses alcohols as starting materials, which is a significant advantage over methods that start from thiols. Alcohols are widely commercially available in a much greater structural diversity than thiols, and they are also nontoxic and not foul-smelling. A reaction mechanism was proposed. A copper-catalysed method for the thioetherification of alcohols with aryl halides using Lawesson's reagent was developed.

Expanding the horizon of intermolecular trapping of in situ generated α-oxo gold carbenes: Efficient oxidative union of allylic sulfides and terminal alkynes via C-C bond formation

With a new P,S-bidentate phosphine as the ligand to gold(i), the α-oxo gold carbenes generated in situ via gold-catalyzed intermolecular oxidation of terminal alkynes were effectively trapped by various allylic sulfides, resulting in the formation of α-aryl(alkyl)thio-γ,δ- unsaturated ketones upon facile [2,3]sigmatropic rearrangements. This journal is the Partner Organisations 2014.

Allylic activation across an Ir-Sn heterobimetallic catalyst: Nucleophilic substitution and disproportionation of allylic alcohol

A nucleophilic substitution of allylic alcohols with carbon (arene, heteroarene, allyltrimethylsilane, and 1,3-dicarbonyl compound), sulfur (thiol), oxygen (alcohol), and nitrogen (sulfonamide) nucleophiles has been demonstrated using an in house developed [Ir(COD)(SnCl3)l(μ-Cl)]2 heterobimetallic catalyst in 1,2-dichloroethane to afford the corresponding allylic products in moderate to excellent yields. In 4-hydroxycoumarin, allylation occurs at the 3-position. The diaryl-substituted allylic alcohols undergo disproportionation in presence of the heterobimetallic catalyst to provide the corresponding alkenes and chalcones. An electrophilic mechanism is proposed from Hammett correlation study.