791-25-3Relevant academic research and scientific papers
A General Protocol for C?H Difluoromethylation of Carbon Acids with TMSCF2Br
Xie, Qiqiang,Zhu, Ziyue,Li, Lingchun,Ni, Chuanfa,Hu, Jinbo
, p. 6405 - 6410 (2019)
An efficient method for the selective C-difluoromethylation of carbon acids with the reagent TMSCF2Br has been developed. A variety of structurally diverse sp3- and sp-hybridized carbon nucleophiles, including esters, amides, fluorenes, terminal alkynes, β-ketoesters, malonates, and other activated C?H nucleophiles, could be efficiently and selectively transformed into the corresponding C-difluoromethylated products under mild conditions. This protocol is also effective for the late-stage difluoromethylation of pharmaceutically relevant molecules and can be readily scaled up. Moreover, ambident substrates with more than one reactive site towards difluorocarbene can be difluoromethylated orthogonally using TMSCF2Br.
Carbon-Selective Difluoromethylation of Soft Carbon Nucleophiles with Difluoromethylated Sulfonium Ylide
Zhu, Jiansheng,Zheng, Hanliang,Xue, Xiao-Song,Xiao, Yisa,Liu, Yafei,Shen, Qilong
supporting information, p. 1069 - 1074 (2018/10/02)
A highly carbon-selective difluoromethylation of soft carbon nucleophiles including β-ketoesters, malonates, oxindoles, benzofuranones and ketene silyl acetals with a difluoromethylated sulfonium ylide under mild conditions was described. Mechanistic studies suggest that these difluoromethylating reactions proceed via a difluorocarbene pathway.
Air- and Light-Stable S-(Difluoromethyl)sulfonium Salts: C-Selective Electrophilic Difluoromethylation of β-Ketoesters and Malonates
Lu, Sheng-Le,Li, Xin,Qin, Wen-Bing,Liu, Jian-Jian,Huang, Yi-Yong,Wong, Henry N. C.,Liu, Guo-Kai
supporting information, p. 6925 - 6929 (2018/10/24)
Air- and light-stable electrophilic difluoromethylating reagents, S-(difluoromethyl)-S-phenyl-S-(2,4,6-trialkoxyphenyl) sulfonium salts were successfully developed, and the introduction of intramolecular hydrogen bonds plays a crucial role for the stabilities and reactivities of these reagents. C-selective difluoromethylation of a broad range of β-ketoesters and malonates proceeded smoothly under mild reaction conditions to give good to excellent yields with excellent C/O regioselectivities.
Utilization of fluoroform for difluoromethylation in continuous flow: A concise synthesis of α-difluoromethyl-amino acids
K?ckinger, Manuel,Ciaglia, Tanja,Bersier, Michael,Hanselmann, Paul,Gutmann, Bernhard,Kappe, C. Oliver
supporting information, p. 108 - 112 (2018/01/12)
Fluoroform (CHF3) can be considered as an ideal reagent for difluoromethylation reactions. However, due to the low reactivity of fluoroform, only very few applications have been reported so far. Herein we report a continuous flow difluoromethyl
A difluoromethylation reagent and a preparing method and applications thereof
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Paragraph 0158; 0236; 0237; 0238; 0239; 0240; 0241; 0242, (2019/01/07)
The invention belongs to the technical field of chemical preparation and particularly relates to a difluoromethylation reagent and preparation and applications thereof. Aiming at a critical problem that electrophilic difluoromethylation reagents at presen
Use of fluoroform as a source of difluorocarbene in the synthesis of N-CF2H heterocycles and difluoromethoxypyridines
Thomoson, Charles S.,Wang, Linhua,Dolbier, William R.
, p. 34 - 39 (2015/03/04)
Fluoroform is used as a source of difluorocarbene to convert various N-, O-, and C-nucleophiles to their difluoromethylated derivatives. Imidazole, benzimidazole, benztriazole, hydroxypyridines, and their derivatives underwent reaction at moderate temperatures and atmospheric pressure, using potassium hydroxide as base in a two-phase (water/acetonitrile) process to provide moderate to good yields of the respective products. Nitrophenols required addition of a co-solvent (methanol) to obtain good yields of products.
Difluoromethylation of some C-H acids with chlorodifluoromethane under conditions of phase transfer catalysis (PTC)
Nawrot, Ewelina,Jończyk, Andrzej
experimental part, p. 466 - 469 (2009/12/05)
Selected C-H acids react with difluorocarbene generated from chlorodifluoromethane with concentrated aqueous solution of sodium hydroxide, and a catalyst, benzyltriethylammonium chloride (TEBAC) in benzene or THF affording C-difluoromethyl substituted der
Reactivity of the Perhalogenoalkanes CF2BrX (X = Cl, Br) with Nucleophiles. Part 4. Condensation with Carbanions
Rico, Isabelle,Cantacuzene, Danielle,Wakselman, Claude
, p. 1063 - 1066 (2007/10/02)
The condensation of CF2BrX (X = Cl, Br) with different carbanions is described.CF2BrX reacts with lithium acetylides and with substituted, active methylene compounds.The limits of reactivity of this reagent as well as the mechanism involved in the condens
