24437-54-5

Upstream product

• 619-41-0 4-(bromoacetyl)toluene 
• 5188-07-8 sodium thiomethoxide 
• 35928-65-5 (methylthio)acetyl chloride 
• 108-88-3 toluene 
• 50609-85-3 (E)-3-methylamino-3-methylthio-1-phenylprop-2-ene-1-thione 
• 17263-64-8 2-diazo-1-(4-methylphenyl)ethanone 
• 2373-51-5 chloro-methylsulfanyl-methane 
• 122334-36-5 N-methoxy-N,4-dimethylbenzamide 
• 122-00-9 para-methylacetophenone 
• 122033-81-2 ω-(Methylthio)-ω-(methylsulfinyl)-p-methylacetophenone 

Downstream Products

• 17293-64-0 (4-methylphenyl)ethynyl methyl sulfide 

Relevant academic research and scientific papers

Thiol-free chemoenzymatic synthesis of β-ketosulfides

A preparation of β-ketosulfides avoiding the use of thiols is described. The combination of a multicomponent reaction and a lipase-catalysed hydrolysis has been developed in order to obtain high chemical diversity employing a single sulfur donor. This methodology for the selective synthesis of a set of β-ketosulfides is performed under mild conditions and can be set up in one-pot two-step and on a gram-scale.

Substituted α-Sulfur Methyl Carbanions: Effective Homologating Agents for the Chemoselective Preparation of β-Oxo Thioethers from Weinreb Amides

The proper generation of α-thiomethyllithium reagents via reductive lithiation or deprotonation followed by reaction with variously functionalized Weinreb amides represents an excellent method to access β-oxo thioethers. The procedure is adaptable to alky

Rh/DuanPhos-Catalyzed Asymmetric Hydrogenation of β-Acetylamino Vinylsulfides: An Approach to Chiral β-Acetylamino Sulfides

Rh/DuanPhos-catalyzed asymmetric hydrogenation of challenging β-acetylamino vinylsulfides has been developed, affording chiral β-acetylamino sulfides with high yields and excellent ee's (up to 99% ee). This novel methodology provides an efficient and concise synthetic route to chiral β-acetylamino sulfides. The potential utility of this protocol in the synthesis of Apremilast has also been disclosed.

One-pot preparation of arylethynyl sulfides and bis(arylethynyl) sulfides

An efficient preparation for arylethynyl sulfides 1 and bis(arylethynyl) sulfides 2 has been accomplished through a one-pot, three-step strategy that starts from arylethanonyl sulfides and bis(arylethanonyl) sulfides, respectively, without the use of various terminal arylacetylenes as substrates. When lithium hexamethyldisilazane (LHMDS), ClP(O)(OEt)2, and LHMDS were sequentially added to a tetrahydrofuran solution of different substrates [arylethanonyl sulfides or bis(arylethanonyl) sulfides], 1 or 2 were obtained in moderate to good yields. The reaction procedure involves the formation of an enol phosphate and a subsequent base-induced elimination. An efficient preparation of arylethynyl sulfides 1 and bis(arylethynyl) sulfides 2 has been accomplished by a one-pot, three-step strategy that starts from arylethanonyl sulfides and bis(arylethanonyl) sulfides, respectively, to give 1 and 2 in moderate to good yields. The reaction mechanism involves the formation of an enol phosphate that undergoes a subsequent base-induced elimination. Copyright

Rhodium(II)-mediated reactions of thiobenzoylketene S,N-acetals with α-diazo carbonyl compounds: Synthesis of 2-substituted 3-alkylamino-5-phenylthiophenes

Treatment of 3-methylamino-3-methylsulfanyl-1-phenylpropenethione 1 with excess (2.5 equiv.) α-diazo carbonyl compounds such as α-diazoketones and α-diazoesters in the presence of a catalytic amount of Rh(II) acetate in CH2Cl2 at rt gave 2-acyl- or 2-aroyl-3-methylamino-5-phenylthiophenes and alkyl 3-methylamino-5-phenylthiophene-2-carboxylates, respectively, as major products along with 1-phenyl-2-methylsulfanylethanones. The formation of the major products indicates that the carbenes or carbenoids generated interact initially with the thione sulfur of 1.

The Electrolytic Reduction of p-Substituted α-(Methylsulfinyl)-α-(methylthio)acetophenones in Acetonitrile

p-Substituted α-(methylsulfinyl)-α-(methylthio)-acetophenones (1) exhibit on polarographic reduction, three wavwes.The two last waves corespond to the reductions of p-substituted α-(methylthio)acetophenones (2) and p-substituted acetophenones respectively

A CONVENIENT GENERAL ACCESS TO α-SULFENYLATED ACETOPHENONES AND ALKANONES

Friedel-Crafts acylation of arenes with methylthio- (1) or phenylthio-acetyl chloride (2) provides ready access to α-methylthio- or α-phenylthio-substituted acetophenones.The acyl chlorides 1 and 2 reacted also with organoaluminium reagents to give α-sulfenylated alkanones.