4148-81-6

Upstream product

• 1459-00-3 1-bromo-2-phenylpropane 
• 108-98-5 thiophenol 
• 106-45-6 para-thiocresol 
• 98-83-9 isopropenylbenzene 
• 882-33-7 diphenyldisulfane 
• 100-68-5 methyl-phenyl-thioether 
• 98-86-2 acetophenone 
• 1123-85-9 (RS)-2-phenyl-1-propanol 

Downstream Products

• 23261-37-2 1-[(E)-1-methyl-2-(phenylsulfanyl)ethenyl]benzene 
• 62924-88-3 (E)-1-methyl-4-(2-phenylprop-1-en-1-yl)benzene 
• 113312-81-5 (Z)-1-methyl-4-(2-phenylprop-1-enyl)benzene 
• 2973-86-6 lithium thiophenoxide 
• 64740-49-4 (2-phenylpropyl)lithium 
• 64740-34-7 1-(2-Phenyl-propyl)-cyclohexanol 
• 4593-90-2 3-phenylbutyric acid 
• 64740-32-5 1,1,3-triphenylbutan-1-ol 

Relevant academic research and scientific papers

Chemoselective Homologation-Deoxygenation Strategy Enabling the Direct Conversion of Carbonyls into (n+1)-Halomethyl-Alkanes

The sequential installation of a carbenoid and a hydride into a carbonyl, furnishing halomethyl alkyl derivatives, is reported. Despite the employment of carbenoids as nucleophiles in reactions with carbon-centered electrophiles, sp3-type alkyl halides remain elusive materials for selective one-carbon homologations. Our tactic levers on using carbonyls as starting materials and enables uniformly high yields and chemocontrol. The tactic is flexible and is not limited to carbenoids. Also, diverse carbanion-like species can act as nucleophiles, thus making it of general applicability.

Stereoselective carbon-carbon bond formation via 1,2-asymmetric induction by a β-substituent in the reaction of α-chloro sulfides with organozinc reagents

The stereoselectivity of C-C bond formation in the reaction of o-chlorosulfides with a variety of organozinc reagents has been investigated. The study reveals excellent 1,2-asymmetric induction by a β-siloxy substituent and moderate 1,2-induction by the β

Hydrothiolation of Alkenes and Alkynes Catalyzed by 3,4-Dimethyl-5-vinylthiazolium iodide and Poly(3,4-dimethyl-5-vinylthiazolium) iodide

The highly selective anti-Markovnikov addition of thiols to unactivated alkenes and alkynes was demonstrated by using 3,4-dimethyl-5-vinylthiazolium iodide or its polymer, poly(3,4-dimethyl-5-vinylthiazolium) iodide, as a complementary catalyst. The reaction proceeded cleanly under base-free conditions in air with both aromatic and aliphatic thiols. The polymer catalyst showed a high turnover number (≈5800) and could be reused up to four times without any loss of catalytic activity. DFT calculations supported stabilization of the thiyl radical intermediate by the thiazolium cation, which resulted in reaction of the radical with unsaturated C?C bonds.

Thiol-ene "click" reaction triggered by neutral ionic liquid: The "ambiphilic" character of [hmim]br in the regioselective nucleophilic hydrothiolation

Thiol-ene "click" chemistry has emerged as a powerful strategy to construct carbon-heteroatom (C-S) bonds, which generally results in the formation of two regioisomers. To this end, the neutral ionic liquid [hmim]Br has been explored as a solvent cum catalyst for the synthesis of linear thioethers from activated and inactivated styrene derivatives or secondary benzyl alcohols and thiols without the requirement of using a metal complex, base, or free radical initiator. Furthermore, detailed mechanistic investigations using 1H NMR spectroscopy and quadrupole time-of-flight electrospray ionization mass spectrometry (Q-TOF ESI-MS) revealed that the "ambiphilic" character of the ionic liquid promotes the nucleophilic addition of thiol to styrene through an anti-Markovnikov pathway. The catalyst recyclability and the extension of the methodology for thiol-yne click chemistry are additional benefits. A competitive study among thiophenol, styrene, and phenyl acetylene revealed that the rate of reaction is in the order of thiol-yne a?a thiol-ene a?a dimerization of thiol in [hmim]Br.

Nickel-catalyzed alkenylative cross-coupling reaction of alkyl sulfides

A novel cross-coupling reaction of alkyl aryl sulfides with aryl Grignard reagents has been achieved to produce the alkenyl-aryl coupling products in high yields by using catalytic Ni(cod)2 and a bulky N-heterocyclic carbene ligand, SIPr.

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.

Water-promoted highly selective anti-Markovnikov addition of thiols to unactivated alkenes

The highly selective anti-Markovnikov addition of thiols to unactivated alkenes is demonstrated in water at room temperature without any additive. This is a very simple and efficient method for the synthesis of linear thioethers. Georg Thieme Verlag Stuttgart.

Indium(I) iodide promoted cleavage of dialkyl/diaryl disulfides and subsequent anti-Markovnikov addition to styrenes: a new route to linear thioethers

The reaction of thiolate anions, generated in situ by indium(I) iodide promoted cleavage of dialkyl/diaryl disulfides, with styrenes has been investigated. Thiolate anions add to a variety of styrenes in an anti-Markovnikov manner producing linear thioethers in high yields. This method provides a new route to the synthesis of thioethers.

Thermolysis of free-radical initiators: tert-butylazocumene and its 1,3- and 1,4-bisazo and 1,3,5-trisazo analogues

Four tert-butylazocumenes (4-7) were prepared from the corresponding cyanobenzenes, and their nitrogen evolution kinetics and products were analyzed. In combination with TEMPO, the simplest compound, tert-butylazocumene (4), shows promise as a "one-radical" initiator of styrene polymerization. The ABNO-trapped cumyl radical 29 is a particularly stable trialkylhydroxylamine, whose thermolysis half-life is 2.1 h at 150 °C. Taking advantage of this stability, we trapped the cumyl radical centers from 7 to afford tris adduct 32a. While the behavior of the meta bisazoalkane 6 can be mostly predicted from that of 4, the para isomer 5 exhibits both unusual products and kinetics, attributed to the formation of quinodimethane 33 via azo-containing radical 34. In fact, flash vacuum pyrolysis of 5 allowed observation of the 1H and 13C NMR spectra of 33, whose persistence even at ambient temperature showed that this quinodimethane is far more stable than the parent 36. Finally, evidence is presented that 7 is an initiator of star polymerization.

Anti-Markovnikov addition of thiols across double bonds catalyzed by H- Rho-zeolite

A variety of olefins react with thiols in the presence of a catalytic amount of H-Rho-zeolite to afford the corresponding anti-Markovnikov addition products in good to excellent yields.