60702-13-8

Usage

InChI:InChI=1/C15H16OS/c1-12(17-15-6-4-3-5-7-15)13-8-10-14(16-2)11-9-13/h3-12H,1-2H3

Upstream product

• 3319-15-1 rac-1-(4-methoxyphenyl)-ethanol 
• 108-98-5 thiophenol 
• 50640-96-5 (R,S)-NN-dimethyl-1-p-methoxyphenylethylamine 
• 882-33-7 diphenyldisulfane 
• 637-69-4 4-Methoxystyrene 
• 32117-52-5 1-(1-(4-methoxyphenyl)ethylidene)-2-tosylhydrazine 
• 27150-99-8 1,1-dimethoxy-1-(4-methoxyphenyl)ethane 
• 6310-14-1 4'-methoxyacetophenone hydrazone 

Downstream Products

• 107270-96-2 1-(1-Benzenesulfonyl-ethyl)-4-methoxy-benzene 
• 107271-01-2 Methanesulfonic acid 1-benzenesulfonyl-1-(4-methoxy-phenyl)-ethyl ester 

Relevant academic research and scientific papers

Transition metal-free coupling reactions of benzylic trimethylammonium salts with di(hetero)aryl disulfides and diselenides

A new protocol was developed to synthesize (enantioenriched) thioethers and selenoethers from (chiral) benzylic trimethylammonium salts and di(hetero)aryl disulfides or diselenides. These syntheses were promoted by the presence of weak base and did not require the use of any transition metal, and resulted in the target products with good to excellent yields (72-94%). Using quaternary ammonium salts synthesized from enantiomerically enriched amines led to highly enantiopure benzylic thioethers and selenoethers (94-99% ee) with configurations reversed from those of their enantioenriched quaternary ammonium salts. This journal is

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.

Eosin-Y-Catalyzed Photoredox C?S Bond Formation: Easy Access to Thioethers

An operationally simple Eosin Y catalyzed sulfenylation of hydrazones has been realized to afford a range of thioethers under visible light. The methodology provides high yields of thioethers under ambient conditions employing readily available and inexpensive starting materials. The reaction has broad substrate scope and is compatible with various functional groups.

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.

Selective synthesis of thioethers in the presence of a transition-metal-free solid Lewis acid

The synthesis of thioethers starting from alcohols and thiols in the presence of amorphous solid acid catalysts is reported. A silica alumina catalyst with a very low content in alumina gave excellent results in terms of both activity and selectivity also under solvent-free conditions. The reaction rate follows the electron density of the carbinol atom in the substrate alcohol and yields up to 99% and can be obtained for a wide range of substrates under mild reaction conditions.

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

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.

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

A novel approach to the practical synthesis of sulfides: An InBr 3-Et3SiH catalytic system promoted the direct reductive sulfidation of acetais with disulfides

We have demonstrated a facile and direct synthesis of sulfide derivatives using acetais and ketals, derived, from aromatic/ conjugated, aldehydes and aromatic ketones, with disulfides and the InBr3-Et3SiH reducing system., We also succeeded in developing an unprecedented one-pot preparation of an aliphatic sulfide from a disulfide and an aliphatic acetal. (Wiley-VCH Verlag GmbH & Co. KGaA.