Sirisuk KeereewanDarunee SoorukramChutima KuhakarnVichai ReutrakulManat PohmakotrMahidol University2019-08-232019-08-232018-01-23European Journal of Organic Chemistry. Vol.2018, No.3 (2018), 295-305109906901434193X2-s2.0-85040838611https://repository.li.mahidol.ac.th/handle/20.500.14594/45511© 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim The synthesis of 3-(1′,1′-difluoroalkyl)-3-hydroxyindolin-2-ones by employing α,α-difluoro-α-phenylsulfanyl-α-trimethylsilylmethane (PhSCF2SiMe3) as a gem-difluoromethylene building block is described. The reaction involves a fluoride-catalyzed nucleophilic addition of PhSCF2SiMe3 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.Mahidol UniversityChemistryArticleSCOPUS10.1002/ejoc.201701106