1333375-53-3Relevant academic research and scientific papers
Synthesis of α-Difluoromethyl Aryl Ketones through a Photoredox Difluoromethylation of Enol Silanes
Arseniyadis, Stellios,Cambeiro, Xacobe C.,Selmi-Higashi, Elias,Zhang, Jinlei
supporting information, p. 4239 - 4243 (2021/06/28)
We report here an efficient and highly straightforward access to α-difluoromethylated ketones through a visible light-mediated difluoromethylation of readily available enol silanes. The method, which takes advantage of the polyvalence of Hu's reagent, N-tosyl-S-difluoromethyl-S-phenylsulfoximine, used here as a CHF2 radical precursor under catalytic photoredox conditions, is practical, scalable, and provides the corresponding α-CHF2 ketones in good to excellent yields.
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.
One-Pot Synthesis of Aryl- and Alkyl S-Perfluoroalkylated NH-Sulfoximines from Sulfides
Chaabouni, Slim,Lohier, Jean-Fran?ois,Barthelemy, Anne-Laure,Glachet, Thomas,Anselmi, Elsa,Dagousset, Guillaume,Diter, Patrick,Pégot, Bruce,Magnier, Emmanuel,Reboul, Vincent
supporting information, p. 17006 - 17010 (2018/10/31)
A general efficient one-pot synthesis of S-perfluoroalkylated NH-sulfoximines from sulfides has been developed using phenyliodine diacetate (PIDA) and ammonium carbamate. Remarkable rate enhancement with trifluoroethanol was observed, presumably due to H-bonding effects. These mild and metal-free conditions are compatible with -CH2F, -CFCl2, -CF2H, -CF2Br, -C4F9, and -CF3 groups, in both the alkyl- and aryl series. Based on a 19F NMR analysis, a λ6-acetoxysulfanenitrile intermediate was proposed.
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 (2015/05/13)
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.
N,N-Dimethyl-S-difluoromethyl-S-phenylsulfoximinium tetrafluoroborate: A versatile electrophilic difluoromethylating reagent
Prakash, G.K. Surya,Zhang, Zhe,Wang, Fang,Ni, Chuanfa,Olah, George A.
experimental part, p. 792 - 798 (2011/10/09)
Over the past decade, sulfur-based fluoromethyl containing compounds have been exhaustively investigated as versatile fluoroalkylating reagents by our research laboratory as well as many others. Lately, we have designed a novel electrophilic difluoromethylating protocol employing in situ prepared N,N-dimethyl-S-difluoromethyl-S-phenylsulfoximinium salt. The present reagent provides excellent reactivity toward a broad spectrum of nucleophilic species (N-, P-, S-, and O-nucleophiles) to yield the corresponding difluoromethylated products with high efficacy under mild conditions. Additional studies have been performed to elucidate the mechanistic fundamentals of the reactions.
