150988-77-5Relevant articles and documents
Palladium-catalyzed cross-coupling of 2,3-naphthoxadisilole with aryl halides
Ding, Han,Chen, Yali,Cao, Weiguo,Wu, Kaicheng,Chen, Jie,Lee, Albert W. M.
, p. 984 - 991 (2010)
Palladium-catalyzed cross-coupling between 2,3-naphthoxadisilole and aryl halides in the presence of tetrabutylammonium fluoride afforded 2-aryl naphthalenes. This is first report that oxadisilole served as a partner in the palladium-catalyzed cross-coupling reactions. The reaction mechanism was also studied.
The suzuki-miyaura reaction performed using a palladium-n-heterocyclic carbene catalyst and a weak inorganic base
Izquierdo, Frédéric,Corpet, Martin,Nolan, Steven P.
, p. 1920 - 1924 (2015)
N-Heterocyclic carbenes (NHCs) have been shown to be useful ligands for the Suzuki-Miyaura cross-coupling at low catalyst loadings. We now report that the commercially available and air-stable [Pd(IPr)(cin)Cl] pre-catalyst permits the formation of various functionalized biaryls from aryl chlorides and boronic acids (37 examples) under very mild conditions using a mixture of ethanol/water as solvent and an inorganic base. [Pd(IPr)(cin)Cl] permits an operationally simple Suzuki-Miyaura reaction under very mild conditions using a mixture of ethanol/water as solvent and an inorganic base.
3,3'-((Arylmethylene)bis(4-methoxy-3,1-phenylene)) dipyridine derivatives as convenient ligands for Suzuki–Miyaura chemo- and homoselective cross-coupling reactions
Hosseini, Raziyeh,Mohammadiannejad, Kazem,Ranjbar-Karimi, Reza
, (2021/08/25)
Four novel N,N-bidentate triarylmethane-based ligands bearing β-pyridyl residues have been prepared and the catalytic activity of their in-situ generated palladium complexes were studied in the Suzuki–Miyaura cross-coupling reactions. Air and moisture stable 3,3'-((arylmethylene)bis(4-methoxy-3,1-phenylene))dipyridines L1-3 showed excellent activity in the Suzuki coupling reactions of aryl halides with aryl boronic acids under thermal and sonochemical reaction conditions. The described methodology provided good to high yields in short reaction times at ambient conditions. Moreover, it offered a straightforward way for Suzuki–Miyaura chemo- and homoselective cross-coupling of aryl halides with phenyl boronic acid. The structures of synthesized compounds were fully characterized by FT-IR, 1H-NMR, 13C-NMR, and elemental analyses. The coordination of palladium acetate to nitrogen sites of L1 was also studied using FTIR spectroscopy, EDX analysis and SEM observations. Graphic abstract: The in-situ generated Pd-complexes of N,N-bidentate ligands L1-3 are described as robust and highly effective catalytic systems for the Suzuki cross-coupling of aryl halides with aryl boronic acids under thermal and sonochemical reaction conditions.[Figure not available: see fulltext.]
Highly active and reusable hydrotalcite-supported Pd(0) catalyst for Suzuki coupling reactions of aryl bromides and chlorides
Karanjit, Sangita,Kashihara, Masaya,Nakayama, Atsushi,Shrestha, Lok Kumar,Ariga, Katsuhiko,Namba, Kosuke
supporting information, p. 948 - 954 (2018/01/27)
A palladium(0) nanocluster supported on hydrotalcite has been prepared and tested for the Suzuki coupling reaction. The prepared catalyst showed very efficient catalytic activity for cross coupling of iodo- and bromoarenes under very mild reaction conditions, affording >90% yield. Under the optimized reaction conditions, chloroarenenes also showed very good reactivity. Transmission electron microscopic imaging data showed the formation of very small Pd(0)-nanoclusters (d = 2.2 ± 0.5 nm) well dispersed on the support, which enhanced the activity and stability of the catalyst for the Suzuki cross-coupling reaction. This catalytic system offers an easy method of preparation with good activity and reusability up to five cycles.
Cyclopalladation in the Periphery of a NHC Ligand as the Crucial Step in the Synthesis of Highly Active Suzuki–Miyaura Cross-Coupling Catalysts
Fizia, Agnes,Gaffga, Maximilian,Lang, Johannes,Sun, Yu,Niedner-Schatteburg, Gereon,Thiel, Werner R.
, p. 14563 - 14575 (2017/10/07)
Starting from 2,4-dichloropyrimidine, 4-(2-dialkylamino)pyrimidinyl functionalized mesitylimidazolium chlorides are accessible in a five-step reaction sequence. Two routes leading to palladium NHC complexes derived from these ligands have been worked out: By transmetalation with the corresponding NHC-AgCl complexes, C,N-coordinated palladium(II) complexes can be obtained. Treatment of palladium dichloride with the imidazolium salts in pyridine and in the presence of K2CO3 gives cyclometalated and thus C,C-coordinated compounds. The reactivities of all these compounds were investigated in detail as well as their performance in the catalytic Suzuki–Miyaura cross-coupling reaction. It turned out that the C,C-coordinated derivatives exhibit high catalytic activities in the coupling of arylboronic acids with aryl chlorides, which is consistent with the generally accepted mechanistic ideas on substrate activation.
