51229-62-0

Upstream product

• 587-04-2 m-Chlorobenzaldehyde 
• 124-38-9 carbon dioxide 
• 63316-58-5 N'-(3-chlorobenzylidene)-4-methylbenzenesulfonohydrazide 
• 108-98-5 thiophenol 
• 1878-65-5 3-chlorophenylacetic acid 

Downstream Products

• 51229-64-2 α-Phenylsulfonyl-α-(3-chlor-phenyl)-essigsaeure 
• 41037-86-9 (α-Jod-3-chlor-benzyl)-phenyl-sulfon 

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.