1097192-99-8Relevant articles and documents
Oxydifluoromethylation of Alkenes by Photoredox Catalysis: Simple Synthesis of CF2H-Containing Alcohols
Arai, Yusuke,Tomita, Ren,Ando, Gaku,Koike, Takashi,Akita, Munetaka
, p. 1262 - 1265 (2016)
We have developed a novel and simple protocol for the direct incorporation of a difluoromethyl (CF2H) group into alkenes by visible-light-driven photoredox catalysis. The use of fac-[Ir(ppy)3] (ppy=2-pyridylphenyl) photocatalyst and shelf-stable Hu's reagent, N-tosyl-S-difluoromethyl-S-phenylsulfoximine, as a CF2H source is the key to success. The well-designed photoredox system achieves synthesis of not only β-CF2H-substituted alcohols but also ethers and an ester from alkenes through solvolytic processes. The present method allows a single-step and regioselective formation of C(sp3)-CF2H and C(sp3)-O bonds from C=C moiety in alkenes, such as hydroxydifluoromethylation, regardless of terminal or internal alkenes. Moreover, this methodology tolerates a variety of functional groups. Light up the bulb! A novel and simple protocol for the direct incorporation of a difluoromethyl (CF2H) group into alkenes by visible-light-driven photoredox catalysis has been developed (see scheme). An Ir photocatalyst is useful for the generation of a CF2H radical through one-electron reduction of Hu's reagent. The present reaction system produces not only various β-CF2H-substituted alcohols, but also ethers and esters in regiospecific manners under mild conditions.
Difluoromethyl and chlorofluoromethyl sulfoximines: Synthesis and evaluation as electrophilic perfluoroalkylating reagents
Pégot, Bruce,Urban, Céline,Bourne, Aaron,Le, Thanh Nghi,Bouvet, Sébastien,Marrot, Jér?me,Diter, Patrick,Magnier, Emmanuel
, p. 3069 - 3075 (2015)
An efficient and convenient method is described that allows the synthesis of a set of difluoromethyl sulfoximines, as well as chlorofluoromethyl sulfoxides, sulfones, and sulfoximines. Our procedure does not require metals or nonrecommended freons, and it gives rise to an original route to Hu's reagent. Unprecedented chlorofluoromethyl sulfoximines have been also isolated, and these compounds have been shown to act as an electrophilic source of this original bis-halogenated moiety. The mechanism of the electrophilic chlorofluoromethylation is also discussed. Bromodifluoromethyl and dichlorofluoromethyl sulfoximines are transformed into the Hu electrophilic difluoromethylating reagent, and into a new chlorofluoromethylating reagent, respectively.
A Unified Strategy for the Synthesis of Difluoromethyl- And Vinylfluoride-Containing Scaffolds
Duchemin, Nicolas,Buccafusca, Roberto,Daumas, Marc,Ferey, Vincent,Arseniyadis, Stellios
supporting information, p. 8205 - 8210 (2019/10/16)
Here, we report a general method for the synthesis of quaternary and tertiary difluoromethylated compounds and their vinylfluoride analogues. The strategy, which relies on a two-step sequence featuring a C-selective electrophilic difluoromethylation and either a palladium-catalyzed decarboxylative protonation or a Krapcho decarboxylation, is practical, scalable, and high yielding. Considering the generality of the method and the attractive properties offered by the difluoromethyl group, this approach provides a valuable tool for late-stage functionalization and drug development.
