80180-01-4Relevant academic research and scientific papers
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.
Well-defined CuC2F5 complexes and pentafluoroethylation of acid chlorides
Panferova, Liubov I.,Miloserdov, Fedor M.,Lishchynskyi, Anton,Martínez Belmonte, Marta,Benet-Buchholz, Jordi,Grushin, Vladimir V.
supporting information, p. 5218 - 5222 (2015/04/27)
Four new well-defined CuI complexes bearing a C2F5 ligand have been prepared and fully characterized: [(Ph3P)2CuC2F5] (2), [(bpy)CuC2F5] (3), [(Ph3P)Cu(phen)C2F5] (4), and [(IPr)CuC2F5] (5). X-ray structures of all four have been determined, showing that the C2F5-ligated Cu atom can be di- (5), tri- (2 and 3), and tetracoordinate (4). The mixed phen-PPh3 complex 4 is a highly efficient fluoroalkylating agent for a broad variety of acid chlorides. This high-yielding transformation represents the first general method for the synthesis of RCOC2F5 from the corresponding RCOCl. Four well-defined CuC2F5 complexes have been prepared and fully characterized, with [(phen)Cu(PPh3)C2F5] (phen=1,10-phenanthroline) proving to be a remarkably efficient fluoroalkylating agent for a broad variety of acid chlorides (see scheme). The procedure represents the first general method for the one-step conversion of RCOCl into valuable pentafluoroethyl ketones.
Enantioselective NHC-Catalyzed Redox [2+2] Cycloadditions with Perfluoroketones: A Route to Fluorinated Oxetanes
Davies, Alyn T.,Slawin, Alexandra M. Z.,Smith, Andrew D.
supporting information, p. 18944 - 18948 (2016/01/26)
The N-heterocyclic carbene (NHC) catalyzed redox formal [2+2] cycloaddition between α-aroyloxyaldehydes and perfluoroketones, followed by ring-opening in situ delivers a variety of perfluorinated β-hydroxycarbonyl compounds in good yield, and excellent diastereo- and enantioselectivity. Through a reductive work-up and subsequent cyclization, this protocol offers access to highly substituted fluorinated oxetanes in two steps and in high ee.
SULFONYL CONTAINING COMPOUNDS AS CYSTEINE PROTEASE INHIBITORS
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Page/Page column 79, (2010/11/24)
The present invention is directed to compounds that are inhibitors of cysteine proteases, in particular, cathepsins B, K, L, F, and S and are therefore useful in treating diseases mediated by these proteases. The present invention is directed to pharmaceutical compositions comprising these compounds and processes for preparing them.
FLUORIDE ION CATALYZED ISOMERIZATION OF 2-ARYL-F-BUTENES
Burton, Donald J.,Headley, James A.
, p. 323 - 356 (2007/10/02)
A kinetic study of the fluoride ion catalyzed isomerization of a series of 2-aryl-F-1-butenes shows the reactions to be pseudo first order in olefin at constant fluoride ion concentration.The resultant Hammett plot is non-linear with a concave downward br
