1333375-53-3Relevant articles and documents
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.
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.
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.