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Advanced Synthesis & Catalysis 09/2010; 352(16):2831 - 2837. · 6.05 Impact Factor
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Angewandte Chemie International Edition 10/2009; 48(45):8551-5. · 13.45 Impact Factor
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ABSTRACT: An efficient preparation of new fluorinated lithium and ammonium sulfonimides, from the corresponding sulfonyl fluorides, is reported. These sulfonyl fluorides are reacted with benzylamine, then triflated. Due to the high leaving ability of fluorinated sulfonimides, the formed N-benzylsulfonimides are simply debenzylated with an alcohol. Finally, the intermediate oxonium sulfonimides are neutralized, in situ, by various bases. The obtained sulfonimides are potential electrolytes for lithium batteries or fuel cells.
The Journal of Organic Chemistry 08/2008; 73(14):5613-6. · 4.45 Impact Factor
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ABSTRACT: An efficient preparation of several polyfluoroalkanesulfonyl fluorides is reported. This method, based on the synthesis of polyfluoroalkyl trimethyl silanes (precursors of polyfluoroalkylsulfinates) as intermediates, allows the successive transformations to be carried out in one pot. Moreover, these sulfonyl fluorides can be obtained from the corresponding sulfinates by electrophilic fluorination. This original approach avoids isolation and purification of some thermally or hydrolytically unstable intermediates. A series of new sulfonyl fluorides have been thus prepared from halogenodifluoromethylated precursors RCF2X (X = F, Br; R = ArC(O), ArS(O)n(CF2)m; n = 0, 1, 2; m = 1, 2) and have been transformed into the corresponding lithium sulfonates, which have potential applications as electrolytes for lithium batteries.
The Journal of Organic Chemistry 12/2007; 72(24):9046-52. · 4.45 Impact Factor
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Annalen der Chemie und Pharmacie 11/2006; 2007(6):891 - 897. · 3.10 Impact Factor
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ABSTRACT: Beta-fluoroalkylated enones are efficient dienophiles in Diels-Alder cycloadditions to prepare various fluorinated cylic compounds. However, the presence of the fluoroalkyl moiety modifies the reactivity and the selectivity of these cycloadditions.
The Journal of Organic Chemistry 04/2006; 71(7):2735-9. · 4.45 Impact Factor
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ABSTRACT: Various trifluoroacetamides and trifluoromethanesulfinamides, derived from chiral silylated amino alcohols, have been synthesized with the goal of achieving enantioselective nucleophilic trifluoromethylation. The best results were obtained with (R)-phenylglycinol derivatives, but the ee values did not exceed 30 %.
Chemistry 02/2005; 11(3):939-44. · 5.93 Impact Factor
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ABSTRACT: The syntheses of various alpha-trifluoromethylated nitrogen heterocycles have been achieved from readily available alpha-(trifluoromethyl)homoallylamine through a ring-closing metathesis.
The Journal of Organic Chemistry 12/2003; 68(23):8932-5. · 4.45 Impact Factor
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Angewandte Chemie International Edition 08/2003; 42(27):3133-6. · 13.45 Impact Factor
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ABSTRACT: Ethers of trifluoroacetaldehyde hemiaminals can undergo dehydrofluorination under basic conditions to provide ethers of difluoroketene hemiaminals. The latter behave as equivalents of difluoroacetamide or difluoroacetate anions towards various electrophiles, yielding a range of difluoromethylcarbonyl products.
Chemistry 08/2002; 8(13):2917-22. · 5.93 Impact Factor
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ABSTRACT: Under Lewis acid activation, hemiaminals of trifluoroacetaldehyde and related (fluoroalkyl)aldehydes generate iminium species that can react with various nucleophiles to provide fluorinated amines.
The Journal of Organic Chemistry 03/2002; 67(3):997-1000. · 4.45 Impact Factor
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ABSTRACT: A new stable hemiaminal of fluoral (1) can easily be obtained from the methyl hemiketal of fluoral and N-benzylpiperazine. This white crystalline compound can be used under basic conditions as an efficient nucleophilic trifluoromethylating reagent towards nonenolizable carbonyl compounds.
Annalen der Chemie und Pharmacie 03/2001; 2001(8):1467 - 1471. · 3.10 Impact Factor
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ABSTRACT: Trifluorothioacetates (CF3CO−S−R, from (CF3CO)2O and thiols) as well as trifluoromethanethio- or trifluoromethaneselenosulfonates (CF3SO2−Y−R; Y = S, Se; from CF3SO2Na, RYYR, and Br2) can be formally decarbonylated or desulfonylated, respectively, provided that they are photolyzed at 40 °C in the presence of 1 equiv of the corresponding disulfide or diselenide. Trifluoromethyl sulfides or selenides are obtained, and the added disulfide (or diselenide) is recovered after reaction. In such a way, S-(trifluoromethyl)cysteine derivatives can be obtained.
04/1999;
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233:968-968.
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65:5361-5368.
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Tetrahedron Letters 37(38):6865-6868. · 2.68 Impact Factor
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Journal of Fluorine Chemistry 131(2):200-207. · 2.03 Impact Factor
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Tetrahedron. 55(26):8065-8074.
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ABSTRACT: Vinylic trifluoromethyl triflones, in particular cyclic ones, constitute potentially valuable building-blocks for further syntheses. Their uses in Diels-Alder cycloadditions as dienophiles or dienes led only to moderate yields of expected products. However, under fluoride activation, they afforded unexpected tricycle compounds.
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ABSTRACT: 4- tert -Butylphenols can be easily transformed into 4-fluorophenols, provided that no coordinating moiety is present in 2-position, in a two step procedure under mild and safe conditions. The first step leads to 4- tert -butyl-4-fluorocyclohexa-2,5-dien-1-ones through an oxidative fluorination with [bis(trifluoroacetoxy)iodo]benzene and triethylamine tris(hydrofluoride), and is followed by an acid catalyzed aromatization with loss of isobutene. When extended to 4- tert -butylacetanilide, this method delivers 4-fluoroacetanilide in a single step but in a modest yield.
