0000000001315041
AUTHOR
Luchao Cui
Etherification of Functionalized Phenols with Chloroheteroarenes at Low Palladium Loading: Theoretical Assessment of the Role of Triphosphane Ligands in CO Reductive Elimination
The present study highlights the potential of robust tridentate ferrocenylphosphanes with controlled conformation as catalytic auxiliaries in CO bond formation reactions. Air-stable palladium triphosphane systems are efficient for selective heteroaryl ether synthesis by using as little as 0.2 mol% of catalyst. These findings represent an economically attractive and clean etherification of functionalized phenols, electron-rich, electron-poor and para-, meta- or ortho-substituted substrates, with heteroaryl chlorides, including pyridines, hydroxylated pyridine, pyrimidines and thiazole. The etherification tolerates very important functions in various positions, such as cyano, methoxy, amino, …
ChemInform Abstract: Thioetherification of Chloroheteroarenes: A Binuclear Catalyst Promotes Wide Scope and High Functional-Group Tolerance.
The nucleophilic substitution of a variety of chloro- and bromohetarenes with arylthiols is optimized to use [PdCl(allyl)]2 in combination with a ferrocenyltetraphosphane as ligand.
Thioetherification of Chloroheteroarenes: A Binuclear Catalyst Promotes Wide Scope and High Functional-Group Tolerance
A constrained binuclear palladium catalyst system affords selective thioetherification of a wide range of functionalized arenethiols with chloroheteroaromatic partners with the highest turnover numbers (TONs) reported to date and tolerates a large variety of reactive functions. The scope of this system includes the coupling of thiophenols with six- and five-membered 2-chloroheteroarenes (i.e., functionalized pyridine, pyrazine, quinoline, pyrimidine, furane, and thiazole) and 3-bromoheteroarenes (i.e., pyridine and furane). Electron-rich congested thiophenols and fluorinated thiophenols are also suitable partners. The coupling of unprotected amino-2-chloropyridines with thiophenol and the s…
CCDC 812731: Experimental Crystal Structure Determination
Related Article: M.Platon, Luchao Cui, S.Mom, P.Richard, M.Saeys, J.-C.Hierso|2011|Adv.Synth.Catal.|353|3403|doi:10.1002/adsc.201100481
CCDC 902497: Experimental Crystal Structure Determination
Related Article: Mélanie Platon, Novi Wijaya, Vincent Rampazzi, Luchao Cui, Yoann Rousselin, Mark Saeys, Jean-Cyrille Hierso|2014|Chem.-Eur.J.|20|12584|doi:10.1002/chem.201403337