Premium
Fluoride‐Catalyzed Nucleophilic Addition of PhSCF 2 SiMe 3 to Isatins: Synthesis of 3‐(1′,1′‐Difluoroalkyl)‐3‐hydroxyindolin‐2‐ones
Author(s) -
Keereewan Sirisuk,
Soorukram Darunee,
Kuhakarn Chutima,
Reutrakul Vichai,
Pohmakotr Manat
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701106
Subject(s) - chemistry , fluoride , isatin , nucleophile , catalysis , yield (engineering) , medicinal chemistry , nucleophilic addition , cleavage (geology) , organic chemistry , inorganic chemistry , materials science , metallurgy , geotechnical engineering , fracture (geology) , engineering
The synthesis of 3‐(1′,1′‐difluoroalkyl)‐3‐hydroxyindolin‐2‐ones by employing α,α‐difluoro‐α‐phenylsulfanyl‐α‐trimethylsilylmethane (PhSCF 2 SiMe 3 ) as a gem ‐difluoromethylene building block is described. The reaction involves a fluoride‐catalyzed nucleophilic addition of PhSCF 2 SiMe 3 to various isatin derivatives followed by the reductive cleavage of the phenylsulfanyl group to lead to 3‐(difluoromethyl)‐3‐hydroxyindolin‐2‐ones in good yields. Under similar reduction conditions but in the presence of activated olefins, an intermolecular radical trapping reaction took place to yield 3‐(1′,1′‐difluoroalkyl)‐3‐hydroxyindolin‐2‐one derivatives.