169059-34-1

Upstream product

• 4848-62-8 Trimethyl(phenylthio)germane 
• 14804-61-6 1-(1-bromoethyl)-4-chlorobenzene 
• 1007-27-8 (phenylthio)trimethylstannane 
• 3391-10-4 1-(p-chlorophenyl)ethyl alcohol 
• 108-98-5 thiophenol 
• 99-91-2 para-chloroacetophenone 
• 75230-50-1 p-chloroacetophenone tosylhydrazone 
• 1073-67-2 4-vinylbenzyl chloride 
• 104-93-8 p-methylanizole 
• 882-33-7 diphenyldisulfane 

Downstream Products

• 20001-65-4 1-chloro-4-(1-chloroethyl)benzene 

Relevant academic research and scientific papers

Molybdenum (VI)-catalyzed dehydrative construction of C[sbnd]O and C[sbnd]S bonds formation via etherification and thioetherification of alcohols and thiols

An inexpensive, easily available, environmentally benign, and efficient catalyst molybdenum(VI) dioxo (acetylacetonate)2 was used for the direct oxo- and thioetherification of alcohol. This method endures selective molybdenum catalyzed dehydrative synthesis of symmetrical ethers from benzylic secondary alcohols as well as unsymmetrical ethers from the reaction of benzylic secondary alcohols with primary alcohol. Furthermore, we have been also successful in the synthesis of Aryl thioether by using alcohol and thiols.

Highly Efficient and Chemoselective Tertiary and Secondary Benzylation of Thiols Catalyzed by Indium(III) Triflate

Several examples of nucleophilic substitution reactions of compounds that have good leaving groups have been previously reported, but the direct use of simple alcohols still remains a challenge because of the poor leaving ability of the hydroxy group. Herein, an efficient and highly chemoselective method for the S-benzylation of a wide range of aromatic and aliphatic thiols has been accomplished in the presence of catalytic amounts (0.1–0.2 mol-%) of indium(III) triflate. Our approach is atom efficient (water is the only byproduct) and suitable to obtain the corresponding unsymmetrical thioethers in excellent yields (up to 99 %). The low loading of catalyst that are needed to obtain extraordinarily high chemoselectivities and the generality of the reaction make this approach unique.

Desulfurative Chlorination of Alkyl Phenyl Sulfides

The chlorination of readily available secondary and tertiary alkyl phenyl sulfides using (dichloroiodo)benzene (PhICl2) is reported. This mild and rapid nucleophilic chlorination is extended to sulfa-Michael derived sulfides, affording elimination-sensitive β-chloro carbonyl and nitro compounds in good yields. The chlorination of enantioenriched benzylic sulfides to the corresponding inverted chlorides proceeds with high stereospecificity, thus providing a formal entry into enantioenriched chloro-Michael adducts. A mechanism implying the formation of a dichloro-λ4-sulfurane intermediate is proposed.

Bimetallic nanosized solids with acid and redox properties for catalytic activation of C-C and C-H bonds

A new approach is presented to form self-supported bimetallic nanosized solids with acid and redox catalytic properties. They are water-, air- and H2-stable, and are able to activate demanding C-C and C-H reactions. A detailed mechanistic study on the formation of the Ag-Fe bimetallic system shows that a rapid redox-coupled sequence between Ag+, O2 (air) and Fe2+ occurs, giving monodisperse Ag nanoparticles supported by O-bridged diatomic Fe3+ triflimides. The system can be expanded to Ag nanoparticles embedded within a matrix of Cu2+, Bi3+ and Yb3+ triflimide.

Iron(III) triflimide as a catalytic substitute for gold(I) in hydroaddition reactions to unsaturated carbon-carbon bonds

In this work it is shown that iron(III) and gold(I) triflimide efficiently catalyze the hydroaddition of a wide array of nucleophiles including water, alcohols, thiols, amines, alkynes, and alkenes to multiple C-C bonds. The study of the catalytic activity and selectivity of iron(III), gold(I), and Bronsted triflimides has unveiled that iron(III) triflimide [Fe(NTf 2)3] is a robust catalyst under heating conditions, whereas gold(I) triflimide, even stabilized by PPh3, readily decomposes at 80 °C and releases triflimidic acid (HNTf2) that can catalyze the corresponding reaction, as shown by in situ 19F, 15N, and 31P NMR spectroscopy. The results presented here demonstrate that each of the two catalyst types has weaknesses and strengths and complement each other. Iron(III) triflimide can act as a substitute of gold(I) triflimide as a catalyst for hydroaddition reactions to unsaturated carbon-carbon bonds. Lewis and Bronsted catalysis: It is shown that iron(III) catalyses as efficiently as gold(I) the hydroaddition of a wide array of nucleophiles, including water, alcohols, thiols, amines, alkynes, and alkenes, to multiple C-C bonds (see scheme). Copyright

Iron-catalysed Markovnikov hydrothiolation of styrenes

The bis(triflimide)iron(III) salt catalyzes the hydrothiolation of styrenes in a Markovnikov fashion with good selectivities and high yields. After isolation, different benzylic thioethers are obtained. This iron(III) catalyst is unique in terms of regioselectivity and represents a sustainable and economic alternative to those processes based on stoichiometric reagents. Copyright

One-pot reductive sulfenylation and thiocyanation of carbonyl compounds in ionic liquid media

The first example of an efficient one-pot reductive sulfenylation and thiocyanation of carbonyl compounds in environmentally benign ionic liquid (IL) media is reported. The process involves reduction of carbonyl compounds with NaBH4 in the IL [bmim]BF4 followed by I2-catalyzed reaction of the resulting alcohols with aromatic/aliphatic thiols or ammonium thiocyanate in the same vessel to afford sulfides or thiocyanates, respectively, in excellent yields (78-93%). Notably, the protocol precludes the necessity to prepare and isolate the intermediate alcohols in a separate step as they are formed in situ, and the IL used can be recycled easily for further use without any loss of efficiency. Copyright

Synthesis of thioethers via metal-free reductive coupling of tosylhydrazones with thiols

A metal-free procedure for the synthesis of thioethers is described via the base-promoted reductive coupling of tosylhydrazones with thiols through an insertion of a carbene into the S-H bond.

The Reaction of (Arylthio)trimethylstannanes with 1-Aryl-1-bromoethanes: Effect of Substituent on the Process Shifting from Unimolecular to Bimolecular Substitution

A kinetic study has been conducted on the reaction of (arylthio)trimethylstannanes with 1-aryl-1-bromoethanes.The reaction of the arylbromoethane bearing an electron-donating substituent was found involving unimolecular ionization of the arylbromoethane.The other reactions, however, were found to be second-order reactions.The nature of the second-order reactions was shifted from one involving unimolecular ionization as the minor process, to a clear bimolecular nucleophilic reaction, according to the electron-withdrawing nature of the substituents on the arylbromoethanes.