14476-62-1

Upstream product

• 25445-77-6 4-phenyl-1,2,3-thiadiazole 
• 75-03-6 ethyl iodide 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 811-51-8 sodium thioethylate 
• 536-74-3 phenylacetylene 
• 110-81-6 Diethyl disulfide 
• 74-96-4 ethyl bromide 
• 64878-58-6 Phosphoric acid diethyl ester (E)-2-ethylsulfanyl-1-phenyl-vinyl ester 
• 70-11-1 α-bromoacetophenone 
• 925-90-6 ethylmagnesium bromide 
• 64846-61-3 phenylacetylenic zinc bromide 
• 33440-88-9 silver phenylacetylide 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 352-93-2 diethyl sulphide 

Downstream Products

• 36814-62-7 phenylethynylthioacetic acid methyl ester 
• 338451-17-5 Toluene-4-sulfonic acid (Z)-1-methylsulfanyl-2-phenyl-vinyl ester 
• 1562258-71-2 C₁₆H₂₃BO₂S 
• 1562258-07-4 C₁₆H₂₃BO₂S 

Relevant academic research and scientific papers

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

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

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

Accessing the Rare Diazacyclobutene Motif

A formal [2 + 2] cycloaddition of 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) with electron-rich alkynyl sulfides and selenides is described. These investigations provide a convenient method to access diazacyclobutenes in good yield while tolerating a rela

A Highly Regio- and Stereoselective Syntheses of α-Halo Enamides, Vinyl Thioethers, and Vinyl Ethers with Aqueous Hydrogen Halide in Two-Phase Systems

A metal-free regio- and stereoselective method is achieved for the preparation of (E)-configured α-halo enamides, vinyl thioethers, and vinyl ethers using aqueous HX (X = F, Cl, Br, I), which features high functional group compatibility and regio- and stereoselectivity, mild conditions, high efficiency, and rapid transformation. Additionally, the isomers could be yielded readily from the (E)-configured α-halo enamides via photocatalysis or under Sonogashira coupling conditions.

Zinc-catalyzed reaction of isoxazoles with thioynol ethers involving an unprecedented 1,2-sulfur migration

A novel zinc-catalyzed reaction of isoxazoles with thioynol ethers involving an unprecedented 1,2-sulfur migration has been developed, which represents the first example of a non-noble metal-catalyzed reaction between isoxazoles and alkynes. This method a

Alkynylthioimidazolium Salts: Efficient Reagents for the Synthesis of Alkynyl Sulfides by Electrophilic Thioalkynylation

The efficient synthesis of a series of alkynylthioimidazolium salts through reaction of organozinc compounds with dibromo(imidazolium)sulfuranes is reported. Addition of Grignard reagents to these new species provided a highly modular, clean, and scalable access to a broad variety of alkynyl sulfides in good-to-excellent yields. The utility of this protocol was showcased by the preparation of alkynyl sulfides, which are particularly difficult to obtain or simply unavailable through the existing methodologies. In addition, the synthetic method was extended to the preparation of alkynyl selenides.

HOTf-Catalyzed, Solvent-Free Oxyarylation of Ynol Ethers and Thioethers

A novel HOTf-catalyzed oxyarylation of ynol ethers and thioethers has been realized with aryl sulfoxides as the oxyarylating reagents, providing α-arylated esters or thioesters in good to excellent yields. Notably, all atoms of the starting materials were incorporated in the product (100% atom economy) and the reaction proceeded under very mild conditions. It was found that the reaction can be ran under air and that the best yields are obtained under solvent-free conditions.

An improved transition-metal-free synthesis of aryl alkynyl sulfides via substitution of a halide at an sp-centre

A simple high-yielding preparation of aryl alkynyl sulfides is presented. The reaction of a chloroacetylene with a thiolate salt in the presence of an amine mediator (dimethylamine or N,N′-dimethylethylenediamine) yields the alkynyl sulfides in excellent yields. The alkynyl chloride is easily prepared from the parent alkyne.

Transition-metal-free synthesis of ynol ethers and thioynol ethers via displacement at sp Centers: A revised mechanistic pathway

We present here valuable extensions to our previous work in preparing highly functionalized, heteroatom-substituted alkynes via displacement at an sp center. Our results show that a wide range of ynol ethers can be prepared by the same methodology and that the same protocol can be applied to the synthesis of synthetically useful thioynol ethers. We also present new observations that have led us to revise our original hypothesis in favor of a pathway involving radical intermediates.