921765-53-9

Upstream product

• 1663-39-4 tert-Butyl acrylate 
• 100-53-8 phenylmethanethiol 
• 921765-54-0 3-benzylsulfanylpropionic acid tert-butyl ester 

Downstream Products

• 833-82-9 (R)-benzyl phenyl sulphoxide 
• 947527-84-6 (R)-1-(benzylsulfinyl)-4-fluorobenzene 
• 287935-43-7 (R)-1-(benzylsulfinyl)-4-nitrobenzene 
• 18506-71-3 1-(benzylsulfinyl)-3-methylbenzene 
• 1365610-84-9 (R)-1-(benzylsulfinyl)-3-methylbenzene 
• 287720-17-6 (R)-(+)-2-naphthyl benzyl sulfoxide 
• 4820-08-0 (R)-1-(benzylsulfinyl)-4-methylbenzene 
• 127594-87-0 benzyl 4-methoxyphenyl sulfoxide 

Relevant academic research and scientific papers

Nondirected Copper-Catalyzed Sulfoxidations of Benzylic C-H Bonds

A copper-catalyzed sulfoxidation of benzylic C-H bonds by nondirected oxidative C(sp3)-H activation was developed. The process proceeds via sulfenate anions, which are generated by base-triggered elimination of β-sulfinyl esters and benzyl radicals. The functional group tolerance is high, and the product yields are good.

Palladium/PC-Phos-Catalyzed Enantioselective Arylation of General Sulfenate Anions: Scope and Synthetic Applications

Herein we reported an efficient palladium-catalyzed enantioselective arylation of both alkyl and aryl sulfenate anions to deliver various chiral sulfoxides in good yields (up to 98%) with excellent enantioselectivities (up to 99% ee) by the use of our developed chiral O,P-ligands (PC-Phos). PC-Phos are easily prepared in short steps from inexpensive commercially available starting materials. The single-crystal structure of the PC4/PdCl2 showed that a rarely observed 11-membered ring was formed via the O,P-coordination with the palladium(II) center. The salient features of this method include general substrate scope, ease of scale-up, applicable to the late-stage modification of bioactive compounds, and the synthesis of a marketed medicine Sulindac.

Aryl sulfoxides via palladium-catalyzed arylation of sulfenate anions

(Chemical Equation Presented) Palladium-catalyzed arylation of sulfenate anions generated from β-sulfinyl esters can take place under biphasic conditions. This hitherto unknown reaction provides a simple, mild, and efficient route to aryl sulfoxides in good yields. The development of a new pseudo-domino type I procedure involving a sulfinylation followed by a Mirozoki-Heck coupling is also described.