41796-43-4

Upstream product

• 673-32-5 1-Phenylprop-1-yne 
• 108-98-5 thiophenol 
• 2327-99-3 1-phenylpropadiene 
• 10147-11-2 propargyl benzene 
• 152959-16-5 (E)-α-bromo-β-phenylthio-β-methylstyrene 
• 882-33-7 diphenyldisulfane 
• 36306-33-9 [2,2-di(phenylsulfanyl)propyl]benzene 
• 137-06-4 2-thiocresol 
• 16158-83-1 (Z)-β-phenylthio-β-methylstyrene 
• 100-52-7 benzaldehyde 
• 13307-56-7 1,1-bis(phenylthio)ethane 
• 38066-16-9 diethyl [(phenylthio)methyl]phosphonate 
• 74-88-4 methyl iodide 
• 121410-99-9 O-<2,2-bis(phenylthio)-1-phenylpropyl> S-methyl dithiocarbonate 

Downstream Products

• 16158-83-1 phenyl (1E)-1-phenylprop-1-en-2-yl sulfide 

Relevant academic research and scientific papers

Synthesis of ketene (S, Te) acetals and their transformation into Z-α- phenylthio-α,β-unsaturated aldehydes

Reaction of thiomethyl phosphonates with aryl (or butyl) tellurenyl halides and aldehydes under basic conditions provides moderate to good yields of ketene thio (telluro) acetals, with vinylic sulfides being byproducts of this transformation. Tellurium-li

Selectivity control in thiol-yne click reactions: Via visible light induced associative electron upconversion

An associative electron upconversion is proposed as a key step determining the selectivity of thiol-yne coupling. The developed synthetic approach provided an efficient tool to access a comprehensive range of products-four types of vinyl sulfides were prepared in high yields and selectivity. We report practically important transition-metal-free regioselective thiol-yne addition and formation of the demanding Markovnikov-type product by a radical photoredox process. The photochemical process was directly monitored by mass-spectrometry in a specially designed ESI-MS device with green laser excitation in the spray chamber. The proposed reaction mechanism is supported by experiments and DFT calculations. This journal is

Highly stereoselective anti-Markovnikov hydrothiolation of alkynes and electron-deficient alkenes by a supported Cu-NHC complex

A practical, efficient, and low-cost heterogeneous catalyst consisting of a Cu-NHC (N-heterocyclic carbene) complex grafted to SBA-15 silica for the catalytic hydrothiolation of alkynes and electron-deficient alkenes under mild reaction conditions has been developed. The heterogeneous catalyst displays higher activity and stereoselectivity to Z-anti-Markovnikov isomers compared with the homogeneous analog under otherwise identical reaction conditions. The catalytic system is applicable to a broad range of alkynes and thiols and is recyclable without significant loss in catalytic performance. High activity and perfect selectivity to alkyl sulfides formed by the addition of electron-deficient alkenes to various thiols catalyzed by the supported Cu-NHC complex were also realized. This journal is the Partner Organisations 2014.

Regio- and stereoselective copper-catalyzed addition of aromatic and aliphatic thiols to terminal and internal nonactivated alkynes

The CuI-catalyzed regio- and stereoselective hydrothio-lation of terminal and internal alkynes affords (Z) - alkenylsulfides. The following isomerization of the Z-isomers into E-isomers catalyzed by CuI is described. Georg Thieme Verlag Stuttgart · New Yo

Alkyne hydrothiolation catalyzed by a dichlorobis(aminophosphine) complex of palladium: Selective formation of cis-configured vinyl thioethers

Cis all round: Dichlorobis[1-(dicyclohexylphosphanyl)piperidine]palladium, [(P{(NC5H10)(C6H11) 2})2Pd(Cl)2], is a highly efficient alkyne hydrothiolation catalyst and the first generally applicable system that selectively generates cis-configured anti-Markovnikov adducts in excellent yields within only a few minutes at 120 °C in the presence of only 0.05 mol % of the catalyst (see scheme).

Highly regio- and stereoselective hydrothiolation of acetylenes with thiols catalyzed by a well-defined supported Rh complex

Highly regio- and stereoselective hydrothiolation of a wide range of alkynes with various thiols was demonstrated in the presence of a well-defined Rh complex supported on mesoporous SBA-15 silica. The catalyst was easily recovered and reused several times without significant loss of activity or selectivity.

Gold-catalyzed regiospecific intermolecular hydrothiolation of allenes

AuBr3-catalyzed regiospecific intermolecular hydrothiolation of aromatic allenes and aromatic thiols afforded the corresponding dithioacetals in good yields at 0°C in 5 min.

Reductive addition of the benzenethiyl radical to alkynes by amine-mediated single electron transfer reaction to diphenyl disulfide

Hydrothiolation of alkynes proceeds with diphenyl disulfide and tripropylamine. Amine-mediated single electron transfer to diphenyl disulfide can be proposed for the reaction mechanism. Applications of the method to radical cyclizations of eneyne compound

Copper-catalyzed synthesis of β-haloalkenyl chalcogenides by addition of dichalcogenides to internal alkynes and its application to synthesis of (Z)-tamoxifen

A copper-catalyzed synthesis of β-haloalkenyl sulfides or selenides was carried out by addition of dichalcogenides and tetrabutylammonium halides to internal alkynes. The present reaction anti- and regio-selectively afforded the corresponding alkenyl chal

Highly regio- and stereocontrolled synthesis of vinyl sulfides via transition-metal-catalyzed hydrothiolation of alkynes with thiols

Regio- and stereoselectivity in the hydrothiolation of alkynes with thiols in the presence of a variety of transition-metal catalysts is investigated in detail. Among the catalysts employed, RhCl(PPh3)3 exhibits excellent catalytic ability toward the anti-Markovnikov addition of thiols (ArSH) to alkynes (RC≡CH), which affords the corresponding vinylic sulfides (trans-RCH=CHSAr) regio- and stereoselectively. The reaction may proceed by the formation of hydrorhodium sulfide species (H-[Rh]-SAr) and probably via the subsequent hydrorhodation of alkynes to provide vinylrhodium intermediates (RCH=CH-[Rh]-SAr). In contrast, PdCl2(PhCN)2-catalyzed hydrothiolation of aromatic alkynes (ArC≡CH) takes place to give the corresponding Markovnikov adducts (R(ArS)C=CH2) with excellent regioselectivity, probably via thiopalladation of alkynes by palladium sulfide species (ArS-[Pd]-Cl), which may be formed by ligand-exchange reaction between PdCl2(PhCN)2 and ArSH. Furthermore, in the case of alkynes bearing propargylic protons (R'CH2C≡CH), a sequential addition/isomerization reaction occurs to provide the internal vinylic sulfides (R'CH=C(SAr)CH3) regioselectively. From the same starting materials (alkyne and thiol), therefore, the regioselectivity of hydrothiolation can be attained simply by changing the catalysts, i.e., RhCl(PPh3)3 and PdCl2(PhCN)2.