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. Pd catalysis was found inevitable for the successful amination of more sterically hindered -(trifluoromethyl)aryl bromides.
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http://dx.doi.org/10.3390/molecules25051084 | DOI Listing |
Sci Rep
January 2025
College of Pharmacy, The Islamic University, Najaf, Iraq.
Palladium nanoparticles were supported on L-H-functionalized KIT-6 (KIT-6@L-H-Pd) and evaluated using various characterization techniques such as TGA, FT-IR, SEM, XRD, EDS, and BET. KIT-6@L-H-Pd showed excellent catalytic performance as a recyclable nanocatalyst for the oxidation of sulfides to sulfoxides and the amination of aryl halides. This approach offers multiple benefits, including the use of readily available and cost-effective materials, a straightforward procedure, short reaction durations, high yields, and a catalyst that is easy to separate and reuse.
View Article and Find Full Text PDFOrg Lett
January 2025
Department of Chemistry, University of Wisconsin-Madison, 1101 University Ave, Madison, Wisconsin 53706, United States.
Although alkyl alcohols and aryl chlorides are the two most abundant substrate pools for cross-electrophile coupling, methods to couple them remain limited. Herein we demonstrate a simple procedure for the in situ deoxychlorination of alcohols followed by XEC with aryl chlorides. A broad substrate scope can be achieved by tuning the rate of the reaction via halide exchange.
View Article and Find Full Text PDFACS Catal
January 2025
Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, United Kingdom.
An aryl radical assay is used to provide information about the formation of aryl radicals from aryl halides in coupling reactions to arenes in the presence of palladium sources and under LED irradiation (λ = 456 nm). The assay uses 2-halo--xylenes as substrates. Aryl radical formation is indicated both by a defined product composition and by signature deuterium isotope effects.
View Article and Find Full Text PDFChemistry
January 2025
Janssen Pharmaceutica NV, chemcial process R&D, BELGIUM.
The manuscript describes the development of an efficient synthetic route to cinnolines, facilitating faster access to JNJ-8003 related Respiratory Syncytial Virus (RSV) non-nucleoside (NNI) inhibitors. Starting from correctly functionalized aryl halides, a Sonogashira reaction followed by SNAr reaction with hydrazine 1,2-dicabroxylate reagents provided dihydrocinnolines directly via in situ 6-endo-dig cyclization. The dihydrocinnolines were conveniently transformed to corresponding cinnolines in one step.
View Article and Find Full Text PDFSci Adv
January 2025
State Key Laboratory of Organometallic Chemistry and Shanghai Hongkong Joint Laboratory in Chemical Synthesis, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China).
Singly occupied molecular orbital (SOMO) activation of in situ generated enamines has achieved great success in (asymmetric) α-functionalization of carbonyl compounds. However, examples on the use of this activation mode in the transformations of other functional groups are rare, and the combination of SOMO activation with transition metal catalysis is still less explored. In the area of deoxygenative functionalization of amides, intermediates such as iminium ions and enamines were often generated in situ to result in the formation of α-functionalized amines.
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