35460-31-2

Usage

Uses

Used in Organic Synthesis:
[(phenylethynyl)sulfanyl]benzene is used as a key intermediate in the synthesis of various organic compounds. Its unique structure allows for a wide range of chemical reactions, making it a valuable component in the development of new molecules and materials.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, [(phenylethynyl)sulfanyl]benzene is used as a building block for the creation of novel drug candidates. Its versatile chemical properties enable the design of molecules with specific biological activities, potentially leading to the development of new treatments for various diseases.
Used in Chemical Research:
[(phenylethynyl)sulfanyl]benzene is also employed in academic and industrial research settings, where it serves as a model compound for studying the properties and reactivity of aromatic compounds with phenylethynyl and sulfanyl groups. This research can contribute to the advancement of chemical knowledge and the discovery of new applications for [(phenylethynyl)sulfanyl]benzene.
Used in Material Science:
[(phenylethynyl)sulfanyl]benzene's unique structure and properties make it a candidate for use in the development of new materials with specific characteristics, such as improved conductivity, stability, or optical properties. These materials could have applications in various industries, including electronics, energy, and environmental protection.

Upstream product

• 6738-06-3 phenylethynylmagnesium bromide 
• 20728-18-1 α-Phenylthiobenzoylmethylenetriphenylphosphorane 
• 85143-07-3 4-Phenyl-5-phenylsulfanyl-[1,2,3]selenadiazole 
• 536-74-3 phenylacetylene 
• 882-33-7 diphenyldisulfane 
• 931-59-9 benzenesulfenyl chloride 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 108-98-5 thiophenol 
• 591-51-5 phenyllithium 
• 53646-00-7 4-phenyl-5-chloro-1,2,3-thiadiazole 
• 108-86-1 bromobenzene 
• 932-88-7 1-iodo-2-phenylethyne 
• 6667-19-2 benzenenesulfenyl dimethylamine 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 

Downstream Products

• 5324-64-1 2-(benzenesulfonyl)ethynylbenzene 
• 1126-80-3 (n-butylthio)benzene 
• 637-44-5 phenylpropyolic acid 
• 109458-94-8 8-Chloro-1-methyl-6-phenyl-7-phenylsulfanyl-bicyclo[3.2.1]oct-6-ene 
• 1612-03-9 3-methyl-1-phenyl-but-1-yne 
• 4250-82-2 (3,3-dimethyl-but-1-ynyl)benzene 
• 33414-83-4 1-(2-cyclohexylethynyl)benzene 
• 536-74-3 phenylacetylene 
• 103-82-2 phenylacetic acid 
• 124-07-2 Octanoic acid 
• 121712-31-0 C₁₉H₁₉ClS 
• 69719-58-0 phenyl(1,2,2-triphenylvinyl)sulfane 
• 18245-74-4 S-phenyl 2-phenylethanethioate 
• 35550-81-3 (2-phenylethene-1,1-diyl)bis(phenylsulfane) 

Relevant academic research and scientific papers

Ru-Catalyzed [3 + 2] Cycloaddition of Nitrile Oxides and Electron-Rich Alkynes with Reversed Regioselectivity

Polarity reversal ("umpolung") of a functional group can override its inherent reactivity and lead to distinct bond-forming modes. Herein we describe a rarely studied cycloaddition between nitrile oxides and electron-rich alkynes with reversed regioselect

Radical-mediated sulfonyl alkynylation, allylation, and cyanation of propellane

Bicyclo[1.1.1]pentane (BCP) is widely applied as the bioisostere for aryl, internal alkynes, andtert-butyl groups in medicinal chemistry. We herein disclose an efficient and practical preparation of sulfonyl alkynyl/allyl/cyano-substituted BCP derivatives

Nickel-Catalyzed Difunctionalization of Alkynyl Bromides with Thiosulfonates and N -Arylthio Succinimides: A Convenient Synthesis of 1,2-Thiosulfonylethenes and 1,1-Dithioethenes

An efficient nickel-catalyzed vicinal thiosulfonylation of 1-bromoalkynes with thiosulfonates in the presence of cesium carbonate is described. An operationally simple and highly regioselective atom transfer radical addition (ATRA) of alkynyl bromides provides a wide range of (E)-1,2-thiosulfonylethenes (α-aryl-β-thioarylvinyl sulfones) in moderate to high yields. The extensive substrate scope of both alkynyl bromides and thiosulfonates is explored with a broad range of functional groups. Indole-derived 1,1-bromoalkenes were also successfully explored in this 1,2-thiosulfonylation process. Moreover, the nickel-catalyzed geminal -dithiolation of alkynyl bromides with N -arylthio succinimides provides 1,1-dithioalkenes in high yields. The present protocol is reliable on gram scale, and a sequential one-pot bromination and thiosulfonylation of phenylacetylene is achieved in a scale-up synthesis. Following control experiments, a plausible mechanism is proposed to rationalize the experimental outcome and the vicinal thio-sulfonylation.

Enantioselective Nickel-Catalyzed Alkyne-Azide Cycloaddition by Dynamic Kinetic Resolution

The triazole heterocycle has been widely adopted as an isostere for the amide bond. Many native amides are α-chiral, being derived from amino acids. This makes α-N-chiral triazoles attractive building blocks. This report describes the first enantioselective triazole synthesis that proceeds via nickel-catalyzed alkyne-azide cycloaddition (NiAAC). This dynamic kinetic resolution is enabled by a spontaneous [3,3]-sigmatropic rearrangement of the allylic azide. The 1,4,5-trisubstituted triazole products, derived from internal alkynes, are complementary to those commonly obtained by the related CuAAC reaction. Initial mechanistic experiments indicate that the NiAAC reaction proceeds through a monometallic Ni complex, which is distinct from the CuAAC manifold.

Synthesis of 2 H-Chromenes via Unexpected [4 + 2] Annulation of Alkynyl Thioethers with o-Hydroxybenzyl Alcohols

A novel Br?nsted acid-catalyzed reaction of alkynyl thioethers with o-hydroxybenzyl alcohols via an unexpected formal [4 + 2] annulation has been developed. This metal-free protocol leads to the facile and practical synthesis of valuable polysubstituted 2

Highly Efficient Enantioselective Synthesis of Chiral Sulfones by Rh-Catalyzed Asymmetric Hydrogenation

A highly efficient and enantioselective Rh-(R,R)-f-spiroPhos complex catalyzed hydrogenation of a series of unsaturated sulfones has been developed. With Rh-(R,R)-f-spiroPhos catalyst under mild conditions, not only the asymmetric hydrogenation of both the 3,3-diaryl and exocyclic α,β-unsaturated sulfones was first realized with up to 99.9% ee but also 3-alkyl-3-aryl and benzo[b]thiophene-1,1-dioxides were successfully hydrogenated to the corresponding chiral sulfones with excellent enantioselectivities (up to 99.4% ee) regardless of the steric hindrance, electronic property, and geometry of the substrates. Moreover, this reaction offers a route to (S)-(+)-ar-turmerone as a spice flavor, which is an important synthetic intermediate of pharmaceuticals.

New arylselanylpyrazole-copper catalysts: Highly efficient catalytic system for C–Se and C–S coupling reactions

We describe herein the use of arylselanylpyrazole–copper complexes as versatile catalysts for C–Se and C–S coupling reactions. The performance of these complexes for C–Se reactions was investigated in chalcogenoacetylene synthesis. The reactions were carried out under mild and aerobic conditions and afforded selanylalkynes bearing a variety of electron-withdrawing and electron-donating groups. The performance of these catalysts for C–S coupling was investigated through the reaction of aryl halides with thiols and products were obtained in moderate to excellent yields. A plausible mechanism for selenoacetylene synthesis is also suggested, and the 77Se NMR results show that these arylselanylpyrazole ligands act as hemilabile ligands. High-resolution mass spectrometry was used to investigate the intermediates and also to corroborate the proposed catalytic cycle.

Rhodium(I)-Catalyzed Regioselective Azide-internal Alkynyl Trifluoromethyl Sulfide Cycloaddition and Azide-internal Thioalkyne Cycloaddition under Mild Conditions

A regioselective method to access fully substituted 5-trifluoromethylthio-1,2,3-triazoles and 5-thio-1,2,3-triazoles from the internal alkynyl trifluoromethyl sulfides and internal thioalkynes by a rhodium(I)-catalyzed azide-alkyne cycloaddition (RhAAC) reaction under mild conditions has been developed. This approach features good compatibility with water and air, a broad substrate scope, good functional group tolerance, high yields and excellent regioselectivities. The high 1,5-regioselectivities were controlled by the strong coordination between the sulfur atom and the π-acidic rhodium. The advantages of this method further include its applicability to gram-scale preparation, the use of solid-phase synthesis technique, and the mutually orthogonal CuAAC-RhAAC reaction. (Figure presented.).

N-Alkynylthio Phthalimide: A Shelf-Stable Alkynylthio Transfer Reagent for the Synthesis of Alkynyl Thioethers

A new kind of electrophilic alkynylthiolating reagent, called N-alkynylthio phthalimide, is designed and synthesized herein. This electrophilic sulfenylating reagent can be easily prepared in three steps from commercially available phthalimide and corresp

Hollow nanoshell-sphere Fe@Fe/Pd reactors: a magnetically recoverable catalyst for the Csp–S cross-coupling reactions in water

The hollow Pd–PVP–Fe nanosphere and Fe–PVP nanoparticle catalysts were synthesized by thermal method. Mixing of two metallic nanocatalysts was applied in the Csp–S cross-coupling reactions between diphenyl disulfide and phenylacetylene under mi