1032154-71-4Relevant articles and documents
Iridium-Catalyzed Transfer Hydrogenation of 1,10-Phenanthrolines using Formic Acid as the Hydrogen Source
Xu, Conghui,Zhang, Lingjuan,Dong, Chaonan,Xu, Jianbin,Pan, Yixiao,Li, Yali,Zhang, Hanyu,Li, Huanrong,Yu, Zhiyong,Xu, Lijin
, p. 567 - 572 (2016)
The iridium-catalyzed highly regioselective transfer hydrogenation of a variety of 2-substituted and 2,9-disubstituted 1,10-phenanthrolines under mild conditions with formic acid as the hydrogen source is described. In the presence of a catalytic amount of the iridium complex [CpIrCl2]2, the transfer hydrogenation proceeded smoothly in 1,4-dioxane under ligand-free conditions, exclusively leading to a range of 1,2,3,4-tetrahydro-1,10-phenanthroline products in high yields. The catalyst generated in situ from [CpIrCl2]2 and (R,R)-(CF3)2C6H3SO2-dpen [N-(2-amino-1,2-diphenylethyl)-3,5-bis(trifluoromethyl)benzenesulfonamide] could efficiently catalyze the asymmetric transfer hydrogenation of these 1,10-phenanthrolines in isopropyl alcohol (i-PrOH) to afford chiral 1,2,3,4-tetrahydro-1,10-phenanthrolines in high yields with up to >99% ee. The key to the success of the reduction is the choice of solvent and hydrogen source.
Br?nsted acid catalyzed asymmetric reduction of 2- and 2,9-substituted 1,10-phenanthrolines
Metallinos, Costa,Barrett, Fred B.,Xu, Shufen
, p. 720 - 724 (2008/12/22)
Several 2- and 2,9-substituted 1,10-phenanthrolines are reduced asymmetrically for the first time using a Hantzsch dihydropyridine in the presence of BINOL-derived phosphoric acid catalysts. The best results are obtained with phenanthrolines bearing unbranched or nitrogen-containing alkyl groups in the 2- or 2,9-positions, which afford chiral octahydrophenanthrolines in a range of yields (40-88%) and good to excellent levels of enantiomeric purity (78-99% ee). Georg Thieme Verlag Stuttgart.
