362-59-4Relevant academic research and scientific papers
An N-Heterocyclic Carbene-Nickel Half-Sandwich Complex as a Precatalyst for Suzuki-Miyaura Coupling of Aryl/Heteroaryl Halides with Aryl/Heteroarylboronic Acids
Ando, Shin,Matsunaga, Hirofumi,Ishizuka, Tadao
, p. 1266 - 1272 (2018/06/18)
A nickel half-sandwich complex supported by our original NHC ligand was developed as a robust precatalyst for Suzuki-Miyaura cross-coupling. The addition of PPh3 was a crucial element in the suppression of side reactions and in accelerating the cross-coupling reaction. By employing the optimal conditions, aryl-aryl, heteroaryl-aryl, and heteroaryl-heteroaryl couplings were achieved.
Transition-Metal-Free Cross-Coupling of Aryl Halides with Arylstannanes
He, Qing,Wang, Liwen,Liang, Yong,Zhang, Zunting,Wnuk, Stanislaw F.
, p. 9422 - 9427 (2016/10/17)
Transition-metal-free LiCl-promoted cross-coupling reactions of tetraphenyltin, trichlorophenyl-, dichlorodiphenyl-, and chlorotriphenylstannanes with aryl halides in DMF provided access to biaryls in good to high yields. Up to four phenyl groups were transferred from the organostannanes substrates. The aryls bearing electron-withdrawing groups in either halides or organotin substrates gave coupling products in higher yields. The methodology has been applied for the efficient synthesis of ipriflavones.
Palladium nanoparticles on graphite oxide as catalyst for Suzuki-Miyaura, Mizoroki-Heck, and Sonogashira reactions
Rumi, Luigi,Scheuermann, Gil M.,Muelhaupt, Rolf,Bannwarth, Willi
experimental part, p. 966 - 976 (2011/08/05)
Pd2+-Exchanged graphite oxide (GO) serves as a precatalyst for the formation of Pd-nanoparticles which are then deposited on the highly functionalized carbonaceous support. This versatile, air-stable, and ligand-free system was applied successfully to Suzuki-Miyaura couplings of some aryl chlorides and to the Mizoroki-Heck as well as the Sonogashira reaction showing relatively high activities and good selectivities. Like with other ligand-free supported systems, the reaction proceeded dominantly by a homogeneous mechanism, but attack of an aryl iodide to Pd-nanoparticles can be excluded as substantial contribution to the entire catalytic process. Beside its straightforward preparation and its stability in air, the system combines the advantages of both homogeneous and heterogeneous catalysis.
Nickel/magnesium-lanthanum mixed oxide catalyst in the Kumada-coupling
Kiss, Arpad,Hell, Zoltan,Balint, Maria
experimental part, p. 331 - 335 (2010/02/16)
A new, heterogeneous, magnesium-lanthanum mixed oxide solid base-supported nickel(ii) catalyst was developed. The catalyst was used successfully in the Kumada coupling of aryl halides, especially aryl bromides. The optimal reaction conditions of the coupling were determined.
Palladium-catalyzed arylation of α,α-disubstituted arylmethanols via cleavage of a C-C or a C-H bond to give biaryls
Terao, Yoshito,Wakui, Hiroyuki,Nomoto, Michiyo,Satoh, Tetsuya,Miura, Masahiro,Nomura, Masakatsu
, p. 5236 - 5243 (2007/10/03)
The palladium-catalyzed arylation of α,α-disubstituted arylmethanols with aryl halides proceeds not only via C-H bond cleavage at the ortho-position, but also via cleavage of the sp2-sp3 C-C bond with the liberation of ketones (β-carbon elimination) to give the corresponding biaryls. Both reactions appear to occur through common arylpalladium(II) alcoholate intermediates. The results of systematic studies with respect to which C-C or C-H bond is preferentially cleaved in the arylation are reported. Among the important findings is the selective elimination of ortho-substituted aryl groups even from aryl(diphenyl)methanols due to steric reasons. Thus, various biaryls having ortho-substituents can be produced efficiently by treatment of the corresponding aryl(diphenyl or dimethyl)methanols with aryl bromides and chlorides.
