Diastereospecific and diastereoselective syntheses of Ruthenium(II) complexes using N,N' bidentate ligands aryl-pyridin-2-ylmethyl-amine ArNH-CH2-2-C5H4N and their oxidation to imine ligands

Inorganic Chemistry
Javier GómezPhillip E Fanwick

Abstract

Coordination of N,N' bidentate ligands aryl-pyridin-2-ylmethyl-amine ArNH-CH2-2-C5H4N 1 (Ar = 4-CH3-C6H4, 1a; 4-CH3O-C6H4, 1b; 2,6-(CH3)2-C6H3, 1c; 4-CF3-C6H4, 1d) to the moieties [Ru(bipy)2]2+, [Ru(eta5-C5H5)L]+ (L = CH3CN, CO), or [Ru(eta6-arene)Cl]2+ (arene = benzene, p-cymene) occurs under diastereoselective or diastereospecific conditions. Detailed stereochemical analysis of the new complexes is included. The coordination of these secondary amine ligands activates their oxidation to imines by molecular oxygen in a base-catalyzed reaction and hydrogen peroxide was detected as byproduct. The amine-to-imine oxidation was also observed under the experimental conditions of cyclic voltammetry measurements. Deprotonation of the coordinated amine ligands afforded isolatable amido complexes only for the ligand (1-methyl-1-pyridin-2-yl-ethyl)-p-tolyl-amine, 1e, which doesn't contain hydrogen atoms in a beta position relative to the N-H bond. The structures of [Ru(2,2'-bipyridine)2(1b)](PF6)2, 2b; [Ru(2,2'-bipyridine)(2)(1c)](PF6)2, 2c; trans-[RuCl2(COD)(1a)], 3; and [RuCl2(eta6-C6H6)(1a)]PF6, 4a, have been confirmed by X-ray diffraction studies.

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Citations

Mar 30, 2007·Chemical Communications : Chem Comm·Hojae Choi, Michael P Doyle
Sep 29, 2007·Journal of Inorganic Biochemistry·Matt L ChildersRoy P Planalp
Nov 10, 2015·Dalton Transactions : an International Journal of Inorganic Chemistry·Jian ZhouLi-Min Zheng
Jun 7, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·Stefan RichterEvamarie Hey-Hawkins
Jun 18, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·S AnjanaNarasimha N Murthy
Dec 17, 2008·Dalton Transactions : an International Journal of Inorganic Chemistry·Jen-Jeh LeeJwu-Ting Chen
Aug 1, 2015·Chemistry : a European Journal·Zhou TangBas de Bruin
Feb 12, 2013·Dalton Transactions : an International Journal of Inorganic Chemistry·Anangamohan Panja, Philippe Guionneau
Jul 19, 2013·Dalton Transactions : an International Journal of Inorganic Chemistry·Rajni K Wilson, Sally Brooker
Oct 19, 2019·Inorganic Chemistry·Mahendra K Awasthi, Sanjay K Singh

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