18053-55-9

Upstream product

• 100-53-8 phenylmethanethiol 
• 754-05-2 ethenyltrimethylsilane 
• 18143-30-1 2-trimethylsilylethanethiol 
• 100-44-7 benzyl chloride 

Downstream Products

• 143505-47-9 benzyl 2-(trimethylsilyl)ethyl sulfoxide 
• 6612-63-1 benzyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 32362-99-5 benzylthioacetate 
• 621-08-9 Dibenzyl sulfoxide 
• 100393-14-4 4-aminophenyl benzyl sulfoxide 
• 18506-73-5 1-(benzylsulfinyl)naphthalene 
• 160480-19-3 benzyl 4-chlorophenyl sulfoxide 
• 2263-73-2 (4-fluorobenzenesulfinylmethyl)benzene 

Relevant academic research and scientific papers

Palladium-Catalyzed Arylation of Alkyl Sulfenate Anions

A unique palladium-catalyzed arylation of alkyl sulfenate anions is introduced that affords aryl alkyl sulfoxides in high yields. Due to the base sensitivity of the starting sulfoxides, sulfenate anion intermediates, and alkyl aryl sulfoxide products, the use of a mild method to generate alkyl sulfenate anions was crucial to the success of this process. Thus, a fluoride triggered elimination strategy was employed with alkyl 2-(trimethylsilyl)ethyl sulfoxides to liberate the requisite alkyl sulfenate anion intermediates. In the presence of palladium catalysts with bulky monodentate phosphines (SPhos and Cy-CarPhos) and aryl bromides or chlorides, alkyl sulfenate anions were readily arylated. Moreover, the thermal fragmentation and the base promoted elimination of alkyl sulfoxides was overridden. The alkyl sulfenate anion arylation exhibited excellent chemoselectivity in the presence of functional groups, such as anilines and phenols, which are also known to undergo palladium catalyzed arylation reactions.

Asymmetric chemical oxidations of aryl and alkyl 2-(trimethylsilyl)ethyl sulfides

A collection of aryl and alkyl 2-(trimethylsilyl)methyl sulfides have been converted to their respective sulfoxides by four different asymmetric oxidizing agents. The chemical yields range from 44-98% while the enantiomeric excesses range from 0-89%. The

Silver fluoroborate promoted sulfur alkylation of β-silyl ethyl sulfides. Selective synthesis of β-thioglycosides

Silver (I) activation of α-glucosyl bromide in the presence of 2-trimethylsilylethyl sulfides as sulfur nucleophiles selectively provides β-thioglycosides.

The reaction of 2-trimethylsilylethyl sulfoxides with sulfuryl chloride. A fragmentation route to sulfinyl chlorides

Sulfinyl chlorides were prepared in good to excellent yields by reacting aryl or alkyl 2-trimethylsilylethyl sulfoxides with SO2Cl2.