An efficient [3 + 2] cycloaddition reaction of difluoromethyl or trifluoromethyl hydrazonoyl bromides with trifluoromethyl-substituted alkenes was investigated to produce a variety of 3,5-bis(fluoroalkyl)pyrazoles/pyrazolines in moderate to good yields. This protocol features obvious advantages such as easily available and stable substrates, step economy, gram-scalability and simple operation, providing a novel and practical method for the preparation of 3,5-bis(fluoroalkyl)pyrazoles/pyrazolines.
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http://dx.doi.org/10.1039/d4ob01160k | DOI Listing |
Org Biomol Chem
November 2024
College of Chemistry and Chemical Engineering, Northwest Normal University, 967 Anning East Road, Lanzhou 730070, P. R. China.
An efficient [3 + 2] cycloaddition reaction of difluoromethyl or trifluoromethyl hydrazonoyl bromides with trifluoromethyl-substituted alkenes was investigated to produce a variety of 3,5-bis(fluoroalkyl)pyrazoles/pyrazolines in moderate to good yields. This protocol features obvious advantages such as easily available and stable substrates, step economy, gram-scalability and simple operation, providing a novel and practical method for the preparation of 3,5-bis(fluoroalkyl)pyrazoles/pyrazolines.
View Article and Find Full Text PDFMolecules
February 2020
Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory, 119991 Moscow, Russia.
The comparison of the possibilities of Pd- and Cu-catalyzed amination reactions using fluorine-containing aryl bromides and iodides with oxadiamines to produce their -diaryl derivatives was carried out. The dependence of the reactivity of the aryl halides on the nature of the substituents and halogen atoms as well as on the structure of oxadiamines was investigated. It was found that the copper-catalyzed reactions were somewhat comparable with the palladium-mediated processes in the majority of cases, especially in the reactions with -fluorine- and -(trifluoromethyl)-substituted aryl halides, although the necessity to use aryl iodides in the Cu(I)-catalyzed amination was obvious.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
April 2019
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA, 02467, USA.
An operationally simple in situ protection/deprotection strategy that significantly expands the scope of kinetically controlled catalytic Z- and E-selective olefin metathesis is introduced. Prior to the addition of a sensitive Mo- or Ru-based complex, treatment of a hydroxy- or a carboxylic-acid-containing olefin with commercially available HB(pin) or readily accessible HB(trip) (pin=pinacolato, trip=2,4,6-tri(isopropyl)phenyl) for 15 min is sufficient for efficient generation of a desired product. Routine workup leads to quantitative deprotection.
View Article and Find Full Text PDFChembiochem
March 2013
Max Planck Institute for Chemical Energy Conversion, Postfach 10135, 45410 Mülheim an der Ruhr, Germany.
Two chemically synthesized flavin derivatives, 8-trifluoromethyl- and 8-bromoriboflavin (8-CF(3)RF and 8-BrRF), were photochemically characterized in H(2)O and studied spectroscopically after incorporation into the LOV domain of the blue light photoreceptor YtvA from Bacillus subtilis. The spectroscopic studies were paralleled by high-level quantum chemical calculations. In solution, 8-BrRF showed a remarkably high triplet quantum yield (0.
View Article and Find Full Text PDFOrg Lett
November 2010
Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan.
The first catalytic enantioselective trifluoromethylation of alkynyl ketones 1 with (trifluoromethyl)trimethylsilane is disclosed by an operationally simple procedure, based on the combination of ammonium bromide of bis-cinchona alkaloids with Me(4)NF to afford trifluoromethyl-substituted tertiary propargyl alcohols (up to 96% ee), which are the important chiral building blocks for pharmaceuticals. Biologically attractive aryl heteroaryl trifluoromethyl carbinols were also synthesized.
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