13479-08-8

Upstream product

• 42253-93-0 (+/-)-2-phenyl-2-phenylsulfanyl-propionic acid ethyl ester 
• 98-86-2 acetophenone 
• 124-38-9 carbon dioxide 
• 4545-21-5 acetophenone p-toluenesulfonylhydrazone 
• 108-98-5 thiophenol 
• 39876-61-4 2-chloro-2-phenyl-propionic acid ethyl ester 
• 2406-23-7 atrolactic acid ethyl ester 
• 515-30-0 2-phenyllactic acid 

Downstream Products

• 42253-92-9 (S)-2-phenyl-2-phenylsulfanyl-propionic acid 
• 14182-43-5 (R)-(-)-2-phenyl-2-(phenylthio)propionic acid 
• 14182-53-7 (R)-2-benzenesulfonyl-2-phenyl-propionic acid amide 
• 42253-93-0 (R)-2-phenyl-2-phenylsulfanyl-propionic acid ethyl ester 
• 14182-59-3 (R)-2-phenyl-2-phenylsulfanyl-propionic acid amide 
• 66693-09-2 (R)-2-benzenesulfonyl-2-phenyl-propionic acid ethyl ester 

Relevant academic research and scientific papers

Umpolung Difunctionalization of Carbonyls via Visible-Light Photoredox Catalytic Radical-Carbanion Relay

The combination of photoredox catalysis with the Wolff-Kishner (WK) reaction allows the difunctionalization of carbonyl groups by a radical-carbanion relay sequence (photo-Wolff-Kishner reaction). Photoredox initiated radical addition to N-sulfonylhydrazones yields α-functionalized carbanions following the WK-type mechanism. With sulfur-centered radicals, the carbanions are further functionalized by reaction with electrophiles including CO2 and aldehydes, whereas CF3 radical addition furnishes a wide range of gem-difluoroalkenes through β-fluoride elimination of the generated α-CF3 carbanions. More than 80 substrate examples demonstrate the broad applicability of this reaction sequence. A series of investigations including radical inhibition, deuterium labeling, fluorescence quenching, cyclic voltammetry, and control experiments support the proposed radical-carbanion relay mechanism.

Stereospecific decarboxylative allylation of sulfones

Allyl sulfonylacetic esters undergo highly stereospecific, palladium-catalyzed decarboxylative allylation. The reaction allows the stereospecific formation of tertiary homoallylic sulfones in high yield. In contrast to related reactions that proceed at -100 °C and require highly basic preformed organometallics, the decarboxylative coupling described herein occurs under mild nonbasic conditions and requires no stoichiometric additives. Allylation of the intermediate α-sulfonyl anion is more rapid than racemization, leading to a highly enantiospecific process. Density functional theory calculations indicate that the barrier for racemization is 9.9 kcal/mol, so the barrier for allylation must be 9.9 kcal/mol.