101068-11-5Relevant articles and documents
A mild and fast photocatalytic trifluoromethylation of thiols in batch and continuous-flow
Straathof, Natan J. W.,Tegelbeckers, Bart J. P.,Hessel, Volker,Wang, Xiao,Nol, Timothy
, p. 4768 - 4773 (2014)
S-CF3 bonds are important structural motifs in various pharmaceutical and agrochemical compounds. However, their preparation remains a major challenge in synthetic organic chemistry. Here, we report the development of a mild and fast photocatalytic trifluoromethylation of thiols. The combination of commercially available Ru(bpy)3Cl2, visible light and inexpensive CF3I gas proved to be an efficient method for the direct trifluoromethylation of thiols. The protocol is demonstrated on a wide range of aromatic, hetero-aromatic and aliphatic substrates in both batch and continuous microflow (32 examples, 52-98% yield). Process intensification through continuous microflow application resulted in a 15-fold increase in production rate (0.25 mmol min-1) due to improved gas-liquid mass transfer, enhanced irradiation as well as convenient handling of the gaseous CF3 source. Furthermore, the efficiency of the flow process allowed to reduce the amount of CF3I (1.1 equivalent) to reach full conversion. This journal is
[[(Ethoxycarbonyl)difluoromethyl]thio]phthalimide: A Shelf-Stable, Electrophilic Reagent with a Convertible Group for the Synthesis of Diversified Fluoroalkylthiolated Compounds
Shen, Feng,Zhang, Panpan,Lu, Long,Shen, Qilong
, p. 1032 - 1035 (2017)
A shelf-stable and easily convertible reagent for the preparation of diversified fluoroalkylthiolated compounds, [[(ethoxycarbonyl)difluoromethyl]thio]phthalimide, was developed. [[(Ethoxycarbonyl)difluoromethyl]thio]phthalimide is an efficient electrophilic fluoroallylthiolating reagent that reacted with electron-rich heteroarenes/arenes, β-ketoesters, oxindoles, benzofuranones, and thiols. More importantly, the ethoxycarbonyl group of the resulting fluoroalkylthiolated compounds could be easily converted into various other functional groups such as chloride, alkynyl, hydrocarbonyl, carbomoyl, hydromethyl, or heteroaryl groups.
Observations on the α-fluorination of α-phenylsulfanyl esters using difluoroiodotoluene
Greaney, Michael F.,Motherwell, William B.
, p. 4463 - 4466 (2000)
α-Phenylsulfanyl esters are fluorinated in the α-position when treated with the hypervalent iodine reagent difluoroiodotoluene. Excess reagent can lead to α-fluoro sulfoxides, which can then undergo thermal syn elimination to produce vinyl fluorides. (C) 2000 Elsevier Science Ltd.
Direct Regioselective [3 + 2] Cycloaddition Reactions of Masked Difluorodiazoethane with Electron-Deficient Alkynes and Alkenes: Synthesis of Difluoromethyl-Substituted Pyrazoles
Zeng, Jun-Liang,Chen, Zhen,Zhang, Fa-Guang,Ma, Jun-An
, p. 4562 - 4565 (2018)
Phenylsulfone difluorodiazoethane (PhSO2CF2CHN2), an easy-to-prepare and bench-stable masked CF2-building block, has been developed. The synthetic utility of this reagent is demonstrated by a direct regioselecti
Alkali Metal Fluorides in Fluorinated Alcohols: Fundamental Properties and Applications to Electrochemical Fluorination
Shida, Naoki,Takenaka, Hiroaki,Gotou, Akihiro,Isogai, Tomohiro,Yamauchi, Akiyoshi,Kishikawa, Yosuke,Nagata, Yuuya,Tomita, Ikuyoshi,Fuchigami, Toshio,Inagi, Shinsuke
, p. 16128 - 16133 (2021)
Fundamental properties of alkali metal fluorides (MF, M = Cs, K) dissolved in 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) or in 3,3,3-trifluoroethanol (TFE) are investigated, including solubility, conductivity, and viscosity. Solid-state structures of single crystals obtained from CsF/HFIP and CsF/TFE are described for the first time, giving insights into the multiple interactions between fluorinated alcohols and CsF. Applications in electrochemical fluorination reactions are successfully demonstrated.
Decarboxylative difluoromethylation of aldehydes with PhSO2CF2COOK: A facile and efficient access to difluoromethylated carbinols
Zhu, Yu-Jun,Lei, Zhong-Liang,Huang, Da-Kang,Lian, Bo,Liu, Zhen-Jiang,Hu, Xiao-Jun,Liu, Jin-Tao
, p. 3184 - 3187 (2018)
A novel decarboxylative difluoromethylation reaction of PhSO2CF2COOK with aldehydes under metal- and ligand-free conditions has been developed. The reaction is very mild and tolerates a wide range of aldehydes (both enolizable and non-enolizable aldehydes), providing a facile and efficient method for the synthesis of structurally diverse difluoromethylated carbinols in moderate to excellent yields.
Catalytic regioselective construction of phenylthio- And phenoxyldifluoroalkyl tetrazoles from difluorodiazoketones
Li, Shuo-Han,Ma, Jun-An,Shi, Hong-Song,Zhang, Fa-Guang
supporting information, p. 13744 - 13747 (2021/12/27)
Here we report the design and synthesis of two new difluoro-diazoketone reagents (difluorophenylthiol diazoketone and difluorophenoxyl diazoketone) and their [3+2] cycloaddition reactions with aryldiazonium salts under silver catalysis conditions. This protocol enables regioselective access to a broad scope of difluorophenylthiol- and difluorophenoxyl-substituted tetrazole-carbinols in a one-pot operation. Further synthetic derivatizations including dephenylthiolation and unexpected phenylthiol group migration/fluorination allow the efficient preparation of α-difluoromethyl tetrazole-carbinols and α-trifluoromethyl tetrazole-thioethers.
Cu(I)-Catalyzed gem-Aminoalkynylation of Diazo Compounds: Synthesis of Fluorinated Propargylic Amines
Pisella, Guillaume,Ramirez, Nieves P.,Waser, Jerome
supporting information, p. 10928 - 10938 (2021/07/31)
The gem-aminoalkynylation of fluorinated diazo compounds catalyzed by a simple Cu(I) salt is described. This three-component reaction allows the synthesis of propargylic amines with broad functional group tolerance. Both electron-rich and electron-poor an
Synthesis method of 1, 1-difluoro-2-isonitrile-ethyl phenyl sulfone compound
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Paragraph 0055-0057, (2020/03/06)
The invention discloses a synthesis method of a 1, 1-difluoro-2-isonitrile-ethyl phenyl sulfone compound. The synthesis method is characterized in that the 1, 1-difluoro-2-isonitrile-ethyl phenyl sulfone compound is synthesized from a 2, 2-difluoro-2-(thi
Efficient asymmetric synthesis of aryl difluoromethyl sulfoxides and their use to access enantiopure α-difluoromethyl alcohols
Batisse, Chloé,Céspedes Dávila, Maria F.,Castello, Marco,Messara, Amélia,Vivet, Bertrand,Marciniak, Gilbert,Panossian, Armen,Hanquet, Gilles,Leroux, Frédéric R.
, p. 3063 - 3079 (2019/05/07)
The -CHF2 moiety has shown a growing interest in pharmaceutical and agrochemical applications over the last few years. Its introduction is therefore a current research topic for organic chemists. Several groups have reported the synthesis of di
