210302-61-7Relevant academic research and scientific papers
Oxidative cross-coupling of ββ-difluoroenol silyl ethers with nucleophiles: A dipole-inversion method to difluoroketones
Uneyama, Kenji,Tanaka, Hiroaki,Kobayashi, Satoru,Shioyama, Manabu,Amii, Hideki
, p. 2733 - 2736 (2004)
Oxidative cross-coupling of α-aryl-β,β-difluoroenol silyl ethers with heteroaromatics in the presence of Cu(OTf)2 in wet acetonitrile proceeds smoothly, affording heteroaryldifluoromethyl aryl ketones in 61-88% yields. Alcohols also react as nu
Base-catalysed 18F-labelling of trifluoromethyl ketones. Application to the synthesis of 18F-labelled neutrophil elastase inhibitors
Meyer, Denise N.,Cortés González, Miguel A.,Jiang, Xingguo,Johansson-Holm, Linus,Pourghasemi Lati, Monireh,Elgland, Mathias,Nordeman, Patrik,Antoni, Gunnar,Szabó, Kálmán J.
supporting information, p. 8476 - 8479 (2021/09/02)
A new method for the fluorine-18 labelling of trifluoromethyl ketones has been developed. This method is based on the conversion of a-COCF3 functional group to a difluoro enol silyl ether followed by halogenation and fluorine-18 labelling. The utility of this new method was demonstrated by the synthesis of fluorine-18 labelled neutrophil elastase inhibitors, which are potentially useful for detection of inflammatory disorders.
Photoredox-catalyzed redox-neutral difluoroalkylation to construct perfluoroketones with difluoroenoxysilanes
Lin, Wu-Jie,Liu, Xue-Yuan,Sun, Wen-Hui,Wang, Yu-Zhao,Zou, Jian-Yu
supporting information, p. 8696 - 8700 (2021/10/22)
A mild and facile approach to construct various perfluoroketonesviaphoto-catalyzed difluoroalkylation of difluoroenoxysilanes is developed. The reaction includes a strategy of combination of two fluorine-containing functional groups, which confers the reaction with characteristics like high efficiency, mild conditions, and broad scope. A variety of fluoroalkyl halides including perfluoroalkyl iodides, bromo difluoro esters and amides can be employed as radical precursors. Control experiments indicate that a single-electron transfer pathway may be involved in the reaction.
Cascade Cyclization of Azadienes with Difluoroenoxysilanes: A One-Pot Formal [4 + 2] Approach to Fluorinated Polyfused Heterocycles
Li, Jinshan,Liu, Saimei,Zhong, Rong,Yang, Yaqi,Xu, Jinjing,Yang, Jianguo,Ding, Hanfeng,Wang, Zhiming
supporting information, p. 9526 - 9532 (2021/12/14)
A TfOH-promoted synthesis of fluorinated polyfused heterocycles via the cascade cyclization of azadienes and difluoroenoxysilanes has been developed, leading to the facile construction of fluorinated benzofuro[3,2-b]pyridines, 5H-indeno[1,2-b]pyridines, and 5,6-dihydrobenzo[h]quinolines. This one-pot formal [4 + 2] approach involves 1,4-difluoroalkylation, desulfonylation, cyclization, and dehydrated and dehydrofluorinated aromatization and represents the first application of difluoroenoxysilane in cascade transformations. Furthermore, this methodology is highlighted by the synthesis of three fluoro analogues of bioactive molecules with potent topoisomerase inhibitory activities.
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.
Mg0-promoted selective C-F bond cleavage of trifluoromethyl ketones: A convenient method for the synthesis of 2,2-difluoro enol silanes
Amii, Hideki,Kobayashi, Takeshi,Hatamoto, Yasushi,Uneyama, Kenji
, p. 1323 - 1324 (2007/10/03)
2,2-difluoro enol silyl ethers were readily prepared by Mg0 promoted selective defluorination of trifluoromethyl ketones in the presence of TMSCI, which involves C-F bond cleavage.
Electroreductive defluorination of trifluoromethyl ketones and trifluoroacetic acid derivatives
Uneyama, Kenji,Mizutani, Go,Maeda, Kazushige,Kato, Tsuyoshi
, p. 6717 - 6723 (2007/10/03)
Difluoroenol silyl ethers 5 and 6, difluoroketene silyl (O,O-, O,S-, and O,N-) acetals 9 and 21, and 2,2-difluoro-2-trimethylsilylacetates 10 were prepared by electroreductive defluorination of trifluoromethyl ketones and trifluoroacetic acid derivatives in an MeCN-TBAB-chlorotrialkylsilane system using a carbon rod as an anode and a lead plate as a cathode. TBAF- or KF- CuI-promoted α-alkylation of 10 with electrophiles such as aldehydes, ketones, imine, acylhalides, and alkylhalides provided α-alkylated-α,α- difluoroacetates in good to excellent yields.
Preparation of 2,2-difluoroenol silyl ethers by electroreductive defluorination of trifluoromethyl ketones
Uneyama, Kenji,Maeda, Kazushige,Kato, Tsuyoshi,Katagiri, Toshimasa
, p. 3741 - 3744 (2007/10/03)
2,2-Difluoroenol silyl ethers (5) were prepared by electroreductive defluorination of trifluoromethyl ketones (4) in the presence of chlorotrialsilanes (TMSCl, TESCl, TBDMSCl).
