121668-44-8Relevant articles and documents
A new,: Substituted palladacycle for ppm level Pd-catalyzed Suzuki-Miyaura cross couplings in water
Takale, Balaram S.,Thakore, Ruchita R.,Handa, Sachin,Gallou, Fabrice,Reilly, John,Lipshutz, Bruce H.
, p. 8825 - 8831 (2019/10/16)
A newly engineered palladacycle that contains substituents on the biphenyl rings along with the ligand HandaPhos is especially well-matched to an aqueous micellar medium, enabling valued Suzuki-Miyaura couplings to be run not only in water under mild conditions, but at 300 ppm of Pd catalyst. This general methodology has been applied to several targets in the pharmaceutical area. Multiple recyclings of the aqueous reaction mixture involving both the same as well as different coupling partners is demonstrated. Low temperature microscopy (cryo-TEM) indicates the nature and size of the particles acting as nanoreactors. Importantly, given the low loadings of Pd invested per reaction, ICP-MS analyses of residual palladium in the products shows levels to be expected that are well within FDA allowable limits.
Phosphino-Triazole Ligands for Palladium-Catalyzed Cross-Coupling
Zhao, Yiming,Van Nguyen, Huy,Male, Louise,Craven, Philip,Buckley, Benjamin R.,Fossey, John S.
supporting information, p. 4224 - 4241 (2018/10/25)
Twelve 1,5-disubtituted and fourteen 5-substituted 1,2,3-triazole derivatives bearing diaryl or dialkyl phosphines at the 5-position were synthesized and used as ligands for palladium-catalyzed Suzuki-Miyaura cross-coupling reactions. Bulky substrates wer
Zwitterionic palladium complexes: Room-temperature Suzuki-Miyaura cross-coupling of sterically hindered substrates in an aqueous medium
Lee, Jhen-Yi,Ghosh, Dabalina,Lee, Jing-Yi,Wu, Shih-Sheng,Hu, Ching-Han,Liu, Shuang-De,Lee, Hon Man
, p. 6481 - 6492 (2015/02/19)
A series of new imidazolium chlorides were straightforwardly prepared from the reactions between chloroacetone and imidazole derivatives. Deprotonation of the methylene proton next to the ketone group in these salts by pyridine led to the formation of a monodentate ligand that coordinated to palladium, readily forming zwitterionic anionic palladium pyridine complexes bearing a formal positive charge on the ligand ancillary. The pyridine ligand in the zwitterionic complexes can be facilely replaced by phosphine ligands. Seven of these new complexes were successfully characterized by X-ray crystallography. The zwitterionic phosphine complexes were highly efficient in catalyzing room-temperature Suzuki-Miyaura reactions between sterically hindered aryl chlorides and arylboronic acids in an aqueous medium.
