347356-46-1Relevant articles and documents
Palladium Complex Immobilized on Magnetic Nanoparticles Modified with 2-Aminopyridine Ligand: A Novel and Efficient Recoverable Nanocatalyst for C–S and C–Se Coupling Reactions
Lu, Lu,Luo, Jia,Wang, Weiqi,Xu, Xiaoqing,Zhang, Jingzheng
, (2022/01/12)
A novel, versatile and efficient magnetically recoverable palladium nanocatalyst [Fe3O4@SiO2/2-aminopyridine-Pd(II)] was fabricated via the immobilization of palladium(II) complex on the surface of magnetic nanoparticles modified with 2-aminopyridine ligand. The structure of the as-fabricated Fe3O4@SiO2/2-aminopyridine-Pd(II) nanocomposite was characterized by a series of spectroscopic techniques including FT-IR, SEM, TEM, EDX, TGA, XRD, VSM and ICP-OES techniques. The Fe3O4@SiO2/2-aminopyridine-Pd(II) nanocomposite was utilized under mild and eco-friendly conditions in C–S and C–Se coupling reactions to afford a vast variety of diaryl sulfides and diaryl selenides with good to excellent yields. This heterogeneous palladium catalyst can be magnetically separated and reused for at least 7 consecutive trials without any reduction in activity. Graphical Abstract: [Figure not available: see fulltext.]
Palladium Nanoparticles Immobilized on Nanosilica Triazine Dendritic Polymer (Pd np -nSTDP) as Catalyst in the Synthesis of Mono-, Di-, and Trisulfides through C-S Cross-Coupling Reactions
Isfahani, Amir Landarani,Mohammadpoor-Baltork, Iraj,Mirkhani, Valiollah,Moghadam, Majid,Khosropour, Ahmad Reza,Tangestaninejad, Shahram,Nasr-Esfahani, Mahboobeh,Rudbari, Hadi Amiri
supporting information, p. 645 - 652 (2014/04/03)
A wide variety of diaryl sulfides has been synthesized in excellent yields via C-S cross-couplings of aryl/heteroaryl halides with aromatic/heteroaromatic thiols in the presence of palladium nanoparticles immobilized on nanosilica triazine dendritic polymer (Pd np -nSTDP) as a reusable catalyst under thermal conditions and microwave irradiation. Pd np -nSTDP also showed excellent catalytic activity for the preparation of a series of di- and trisulfides with benzene, pyridine, pyrimidine, and/or 1,3,5-triazine as the central cores by one-pot multi C-S cross-coupling reactions. Georg Thieme Verlag Stuttgart. New York.
Development of a new variant of the migita reaction for carbon#sulfur bond formation used in the manufacture of tetrahydro-4-[3-[4-(2-methyl-1H-imidazol-1- yl)phenyl]thio]phenyl-2H-pyran-4-carboxamide
Norris, Timothy,Leeman, Kyle
supporting information, p. 869 - 876 (2013/01/03)
Palladium-catalyzed carbon-sulfur bond formation using modified Migita reaction conditions was explored and applied to the synthesis of a former antiasthma drug candidate, tetrahydro-4-[3-[4-(2-methyl-1H-imidazol-1-yl)phenyl] thio]phenyl-2H-pyran-4-carboxamide (5). The reaction was developed into a general method for thioaryl halide cross-coupling, and a specific example of its use to synthesize a key intermediate, tetrahydro-4-[3-(4-fluorophenyl)thio] phenyl-2H-pyran-4-carboxamide (6) was demonstrated at large scale to provide phase II clinical supplies of 5. Comparison of the multistep phase I process and the two-step phase II process showed an overall yield advantage over the bond-forming steps from common starting material (1) to API 5 of 40%. The ligand effect in the modified Migita reaction is described in detail. The second step of the scale-up process illustrated formation of carbon-nitrogen bonds without use of palladium catalysis, providing a contrast to the first reaction; both reactions were developed into efficient single-vessel direct isolation processes.
