42442-47-7

Upstream product

• 110-06-5 di-tert-butyl disulfide 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 42599-24-6 E-styryl iodide 
• 75-66-1 2-methylpropan-2-thiol 
• 536-74-3 phenylacetylene 
• 102-96-5 (2-nitroethenyl)benzene 
• 103-64-0 bromostyrene 
• 42442-46-6 (Z)-1-phenyl-2-(tert-butylthio)ethene 
• 932-88-7 1-iodo-2-phenylethyne 
• 932-87-6 1-Bromo-2-phenylacetylene 

Relevant academic research and scientific papers

A New Tin Mediated Pummerer Synthesis of Vinyl Stannanes

Treatment of a range of sulfoxides with 3 equivalents of LDA and 6 equivalents of tri-n-butyltin chloride yields the corresponding α-tributylstannyl vinyl sulfides in good yield. When a tert-butyl sulfoxide is used the α-tributylstannyl vinyl sulfide is isolated as a single geometric isomer.

Electrophilic Vinylation of Thiols under Mild and Transition Metal-Free Conditions

The iodine(III) reagents vinylbenziodoxolones (VBX) were employed to vinylate a series of aliphatic and aromatic thiols, providing E-alkenyl sulfides with complete chemo- and regioselectivity, as well as excellent stereoselectivity. The methodology displays high functional group tolerance and proceeds under mild and transition metal-free conditions without the need for excess substrate or reagents. Mercaptothiazoles could be vinylated under modified conditions, resulting in opposite stereoselectivity compared to previous reactions with vinyliodonium salts. Novel VBX reagents with substituted benziodoxolone cores were prepared, and improved reactivity was discovered with a dimethyl-substituted core.

N-heterocyclic carbene-catalyzed regio- and stereoselective hydrothiolation reaction of alkynes

N-heterocyclic carbenes (NHCs) have been utilized as Br?nsted base to catalyze the hydrothiolation reaction between alkynes and thiols to produce the vinyl sulfides stereoselectively.

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.

Straightforward and highly efficient catalyst-free regioselective reaction of thiol to β-nitrostyrene: a concise synthesis of vinyl sulfide and nitro sulfide

Under catalyst-free reaction conditions, solvent-mediated addition of thiol 2 to β-nitrostyrene 1 proceeded with regioselective control to afford either adduct 3 or vinyl sulfide 4 in good to excellent yield. Thermodynamic and autocatalytic reaction mecha

Ionic liquid promoted regio- And stereoselective addition of thiols to alkynes and alkenes under organic solvent free condition - A green reaction

A simple ionic liquid, l-methyl-3-pentylimidazolium fluoroborate, [pmIm]BF4, promotes anti-Markovnikov addition of thiols to alkynes providing (Z)- and (E)-vinyl sulfides stereoselectively. The addition of thiols to alkenes in presence of another ionic liquid, [pmim]Br proceeds through anti-Markovnikov manner, whereas the addition to vinyl ethers and acetates occurs at more electrophilic C-2 position adjacent to oxygen. The products are obtained in high yields.

Stereo-recognizing transformation of (E)-alkenyl halides into sulfides catalyzed by nickel(0) triethyl phosphite complex

(E)-Alkenyl halides were transformed into (E)-alkenyl sulfides by the nickel(0) triethyl phosphite complex-catalyzed reaction with thiols, whereas (Z)-alkenyl halides gave alkynes under the same reaction conditions. Aryl halides were also transformed into aryl sulfides using the same reagent system.

Copper-catalyzed synthesis of vinyl sulfides

(Chemical Equation Presented) We report a method for the synthesis of vinyl sulfides using the soluble copper(I) catalyst [Cu(phen)(PPh3) 2]NO3. The desired vinyl sulfides are obtained in good to excellent yields, with retention of stereochemistry. This protocol tolerates a wide variety of functional groups or substrates, is palladium-free, and does not require the use of expensive or air-sensitive additives.

A Direct Formation of Alkenyl Chalcogenides from Nonactivated Alkenyl Halides and Diorganyl Dichalcogenides under Neutral Conditions

Alkenyl sulfides and selenides were easily obtained in moderate to good yields by heating the corresponding bromides with diorganyl disulfides or diselenides in hexamethylphosphoric triamide with or without copper(I) iodide as a promoter.