Cu(I)- and Pd(0)-Catalyzed Arylation of Oxadiamines with Fluorinated Halogenobenzenes: Comparison of Efficiency

Lyakhovich, M. S.; Averin, Alexei D.; Grigorova, O. K.; Roznyatovsky, Vitaly A.; Maloshitskaya, O. A.; Beletskaya, I. P.

doi:10.3390/molecules25051084

Cited by 7 publications

(4 citation statements)

References 31 publications

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“…Copper-catalyzed C-N coupling reactions have been extensively studied [ 29 ], and Buchwald has reportedly implemented this type of reaction using bromo- or iodobenzenes as substrates progressively, but not with five-membered heterocyclic compounds such as pyrazoles [ 30 , 31 , 32 , 33 , 34 , 35 , 36 ]. As the C-N coupling reaction of 4-halopyrazoles 1 with allyl- or alkylamines bearing β-hydrogen atoms revealed low reactivities in the above investigation ( Table 2 , entries 4–12), the copper-catalyzed reaction of 1 was further studied.…”

Section: Resultsmentioning

confidence: 99%

C4-Alkylamination of C4-Halo-1H-1-tritylpyrazoles Using Pd(dba)2 or CuI

et al. 2020

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Alkylamino coupling reactions at the C4 positions of 4-halo-1H-1-tritylpyrazoles were investigated using palladium or copper catalysts. The Pd(dba)2 catalyzed C-N coupling reaction of aryl- or alkylamines, lacking a β-hydrogen atom, proceeded smoothly using tBuDavePhos as a ligand. As a substrate, 4-Bromo-1-tritylpyrazole was more effective than 4-iodo or chloro-1-tritylpyrazoles. Meanwhile, the CuI mediated C-N coupling reactions of 4-iodo-1H-1-tritylpyrazole were effective for alkylamines possessing a β-hydrogen atom.

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Section: Resultsmentioning

confidence: 99%

C4-Alkylamination of C4-Halo-1H-1-tritylpyrazoles Using Pd(dba)2 or CuI

et al. 2020

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“…However, the possibilities of C-N -based multiple cross-couplings of polychlorinated benzenes were never studied in detail according to our best knowledge. Merely differences in cross-couplings of aromates substituted with different halides (typically bromoiodobenzenes, bromo-chlorobenzenes and halogeno-fluorobenzenes) were mentioned in published articles [59,60,70,[128][129][130][131][132][133][134][135].…”

Section: Discussionmentioning

confidence: 99%

Copper-Catalyzed Reactions of Aryl Halides with N-Nucleophiles and Their Possible Application for Degradation of Halogenated Aromatic Contaminants

2022

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This review summarizes recent applications of copper or copper-based compounds as a nonprecious metal catalyst in N-nucleophiles-based dehalogenation (DH) reactions of halogenated aromatic compounds (Ar-Xs). Cu-catalyzed DH enables the production of corresponding nonhalogenated aromatic products (Ar-Nu), which are much more biodegradable and can be mineralized during aerobic wastewater treatment or which are principally further applicable. Based on available knowledge, the developed Cu-based DH methods enable the utilization of amines for effective cleavage of aryl-halogen bonds in organic solvents or even in an aqueous solution.

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“…We investigated the N,N′-diarylation of three different oxadiamines, 218-220, varying their length, and number of oxygen atoms and methylene groups between N and O atoms (Scheme 17) [140]. CuI/L1 in DMF was shown to be the most active catalytic system, and trioxadiamine 218 was reacted with a large series of aryl iodides.…”

Section: Nn′-diarylation Of the Di-and Polyamines Using Cu(i) Catalysismentioning

confidence: 99%

Recent Achievements in the Copper-Catalyzed Arylation of Adamantane-Containing Amines, Di- and Polyamines

et al. 2023

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Rapid development of the copper-catalyzed amination of aryl halides in the beginning of the 21st century, known as the Renaissance of the Ullmann chemistry, laid foundations for the use of this method as a powerful tool for the construction of the C(sp2)-N bond and became a rival of the Buchwald–Hartwig amination reaction. Various applications of this approach are well-documented in a number of comprehensive and more specialized reviews, and this overview in the form of a personal account of the Cu-catalyzed arylation and heteroarylation of the adamantane-containing amines, and di- and polyamines, covers a more specific area, showing the possibilities of the method and outlining general regularities, considering reagents structure, copper source and ligands, scope, and limitations. The material of the last decade is mainly considered, and recent data on the application of the unsupported copper nanoparticles and possibilities of the Chan-Lam reaction as an alternative to the use of aryl halides are also discussed.

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Cu(I)- and Pd(0)-Catalyzed Arylation of Oxadiamines with Fluorinated Halogenobenzenes: Comparison of Efficiency

Cited by 7 publications

References 31 publications

C4-Alkylamination of C4-Halo-1H-1-tritylpyrazoles Using Pd(dba)2 or CuI

C4-Alkylamination of C4-Halo-1H-1-tritylpyrazoles Using Pd(dba)2 or CuI

Copper-Catalyzed Reactions of Aryl Halides with N-Nucleophiles and Their Possible Application for Degradation of Halogenated Aromatic Contaminants

Recent Achievements in the Copper-Catalyzed Arylation of Adamantane-Containing Amines, Di- and Polyamines

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