92497-27-3

Upstream product

• 100-53-8 phenylmethanethiol 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 150-60-7 dibenzyl disulphide 
• 1004-22-4 (phenylethynyl)sodium 
• 35460-31-2 (2-phenylsulfanylethynyl)benzene 
• 3012-37-1 benzyl thiocyanate 
• 536-74-3 phenylacetylene 
• 100-39-0 benzyl bromide 
• 1483-82-5 phenylethynyl chloride 
• 16601-02-8 S-benzyl 4-methylbenzenethiosulfonate 
• 20568-13-2 lithium 2-phenylethynethiolate 

Downstream Products

• 77128-62-2 2-(benzylthio)-3-phenylbenzo[b]thiophene 
• 1418295-28-9 C₃₃H₁₂BF₁₅S 
• 13294-33-2 (Z)-styryl benzylsulfide 
• 1562258-41-6 C₂₁H₂₅BO₂S 
• 1562258-89-2 C₂₁H₂₅BO₂S 
• 1428318-79-9 1-benzyl-5-(benzylthio)-4-phenyl-1H-1,2,3-triazole 
• 1432187-45-5 C₂₂H₁₇NOS 
• 929692-42-2 1-benzylsulfinyl-2-phenylacetylene 

Relevant academic research and scientific papers

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

Chemo- And regioselective click reactions through nickel-catalyzed azide-alkyne cycloaddition

Metal-catalyzed cycloaddition is an expeditious synthetic route to functionalized heterocyclic frameworks. However, achieving reactivity-controlled metal-catalyzed azide-alkyne cycloadditions from competing internal alkynes has been challenging. Herein, we report a nickel-catalyzed [3 + 2] cycloaddition of unsymmetrical alkynes with organic azides to afford functionalized 1,2,3-triazoles with excellent regio- and chemoselectivity control. Terminal alkynes and cyanoalkynes afford 1,5-disubstituted triazoles and 1,4,5-trisubstituted triazoles bearing a 4-cyano substituent, respectively. Thioalkynes and ynamides exhibit inverse regioselectivity compared with terminal alkynes and cyanoalkynes, affording 1,4,5-trisubstituted triazoles with 5-thiol and 5-amide substituents, respectively. Density functional theory calculations are performed for the elucidation of the reaction mechanism. The computed mechanism suggests that a nickellacyclopropene intermediate is generated by the oxidative addition of the alkyne substrate to the Ni(0)-Xantphos catalyst, and the subsequent C-N coupling of this intermediate with an azide is responsible for the chemo- and regioselectivity.

Convenient and Efficient Diastereoselective Preparation of Functionalized Z-Alkenyl Sulfides

We have developed an efficient and convenient regio- and stereoselective reduction of the alkynyl sulfides with pinacolborane in the presence of copper(I) chloride to produce (Z)-alkenyl sulfides in good and very good yields. The functionalized alkynyl sulfides are readily available based on the reaction of lithium acetylides with thiotosylates under mild 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

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

Synthesis of Isothiochroman-3-ones via Metal-Free Oxidative Cyclization of Alkynyl Thioethers

A novel Br?nsted acid-catalyzed oxidative C-H functionalization of alkynyl thioethers has been developed. This method allows the practical synthesis of valuable isothiochroman-3-ones in mostly moderate to good yields under mild reaction conditions and features a broad substrate scope and wide functional group tolerance. Moreover, this metal-free oxidation can also be used to promote formal N-H insertion involving an unexpected 1,2-sulfur migration, affording useful 1,4-benzothiazin-3-ones.

Approach for 2-(arylthio)imidazoles and imidazo[2,1-b]thiazoles from imidazo[2,1-b][1,3,4]thiadiazoles by ring-opening and -reconstruction

A highly efficient one-pot synthesis of imidazo[2,1-b]thiazole derivatives has been developed and proceeds via a ring-opening and ring-closing reconstruction of imidazo[2,1-b][1,3,4]thiadiazoles with phenylacetylene in the presence of potassium tert-butox

Lewis acid-promoted hydrofluorination of alkynyl sulfides to generate α-fluorovinyl thioethers

A new method for the preparation of α-fluorovinyl thioethers is reported which involves the hydrofluorination of alkynyl sulfides with 3HF·Et3N, a process that requires Lewis acid activation using BF3·Et2O and TiF4/s

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.