395-01-7Relevant articles and documents
Solvent dependence of the synthesis and reactions of acetyl hypofluorite
Rozen, Shlomo,Bareket, Yifat,Kol, Moshe
, p. 141 - 146 (1993)
Acetyl hypofluorite (AcOF) has been previously prepared using CFCl3 (CFC-11) as a solvent.It was found that acetonitrile can replace trichlorofluoromethane without sacrificing the efficiency and the regio- and stereo-selectivity of the addition of AcOF to olefins.Most other solvents tested proved to be inadequqte for the synthesis of AcOF, despite the fact that fluorine does react with the dispersed sodium acetate present in the solvent.
Palladium-catalyzed one-pot construction of difluorinated 1,3-enynes from α,α,α-iododifluoroacetones and alkynes
Wang, Xing,Hu, Jian,Ren, Jie,Wu, Tianci,Wu, Jingjing,Wu, Fanhong
, (2019)
A palladium-catalyzed one-pot difunctionalization of alkynes with α,α,α-iododifluoroacetones is introduced for the synthesis of difluorinated 1,3-enynes. The reaction proceeds through the radical addition of RCOCF2 radical to alkynes and subseq
Single electron transfer approaches to the practical synthesis of aromatic and heterocyclic-CF2H derivatives
Dolbier Jr., William R,Médebielle, Maurice,Ait-Mohand, Samia
, p. 4811 - 4814 (2001)
Single electron transfer (SET) approaches with organic reductants such as sodium hydroxymethanesulfinate (Rongalite), sodium dithionite (regarded as precursors of sulfoxylate radical anion) and tetrakis(dimethylamino)ethylene (TDAE) were employed for the reductive dehalogenation of a series of halogeno-difluoromethylated aromatics and heterocycles, and for the practical synthesis of the corresponding difluoromethylated derivatives.
Direct Synthesis of Tri-/Difluoromethyl Ketones from Carboxylic Acids by Cross-Coupling with Acyloxyphosphonium Ions
Ispizua-Rodriguez, Xanath,Munoz, Socrates B.,Krishnamurti, Vinayak,Mathew, Thomas,Prakash
supporting information, p. 15908 - 15913 (2021/10/07)
A simple and straightforward approach to the synthesis of trifluoromethyl and difluoromethyl ketones from widely available carboxylic acids is disclosed. The transformation utilizes an acyloxyphosphonium ion as the active electrophile, conveniently generated in situ from the carboxylic acid substrate by using commodity chemicals. The utility of the reaction system is exemplified by its chemoselectivity, with tolerance to a variety of important functional groups. The late-stage functionalization of carboxylic acid active pharmaceutical ingredients and pharmaceutically relevant compounds is also discussed.
Trifluoromethylthiolation, Trifluoromethylation, and Arylation Reactions of Difluoro Enol Silyl Ethers
Jiang, Xingguo,Meyer, Denise,Baran, Dominik,Cortés González, Miguel A.,Szabó, Kálmán J.
, p. 8311 - 8319 (2020/07/16)
This study reports a new application area of difluoro enol silyl ethers, which can be easily obtained from trifluoromethyl ketones. The main focus has been directed to the electrophilic fluoroalkylation and arylation methods. The trifluoromethylthiolation of difluoro enol silyl ethers can be used for the construction of a novel trifluoromethylthio-α,α-difluoroketone (-COCF2SCF3) functionality. The -CF2SCF3 moiety has interesting properties due to the electron-withdrawing, albeit lipophilic, character of the SCF3 group, which can be combined with the high electrophilicity of the difluoroketone motif. The methodology could also be extended to difluoro homologation of the trifluoromethyl ketones using the Togni reagent. In addition, we presented a method for transition-metal-free arylation of difluoro enol silyl ethers based on hypervalent iodines.