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Abstract
Reaction of Ru3(CO)12 with two equiv of 6-bromopyridine alcohols 6-bromopyCHROH [(R = C6H5 (L1); R = 4-CH3C6H4 (L2); R = 4-OMeC6H4 (L3); R = 4-ClC6H4 (L4); (R = 4-CF3C6H4 (L5); R = 2-OMeC6H4 (L6); R = 2-CF3C6H4 (L7)] and 6-bromopyC(Me)2OH (L8) in refluxing xylene afforded novel trinuclear ruthenium complexes [6-bromopyCHRO]2Ru3(CO)8 (1a-1g) and [6-bromopyC(Me)2O]2Ru3(CO)8 (1h). These complexes were characterized by FT-IR and NMR spectroscopy as well as elemental analysis. The structures of all the complexes were further confirmed by X-ray crystallographic analysis. In the presence of tert-butyl hydroperoxide (TBHP) as the source of oxidant, complexes 1a-1h displayed high catalytic activities for oxidation of primary and secondary alcohols and most of oxidation reactions could be completed within 1 h at room temperature.
Highlights
As a class of common starting materials, alcohols can beeasily converted into a variety of useful compounds via organic synthesis methods (Salvatore et al, 2001; Crabtree, 2017)
As part of our continuing efforts in developing novel ruthenium carbonyl complexes and their applications in alcohol oxidation, we reported the synthesis and characterization of several ruthenium carbonyl complexes supported by pyridinealkoxide ligands and their catalytic properties in the oxidation of primary and secondary alcohols using tert-butyl hydroperoxide (TBHP) as an oxidant
6-bromopyridine alcohol ligands L1-L6 and L8 were synthesized according to the literature procedure (Tsukahara et al, 1997; Song and Morris, 2004) and identified by NMR and elemental analysis prior to use
Summary
As a class of common starting materials, alcohols can beeasily converted into a variety of useful compounds via organic synthesis methods (Salvatore et al, 2001; Crabtree, 2017). Conventional oxidation methods to access these compounds usually require stoichiometric amounts of inorganic oxidants, such as chromium(VI) compounds (Canielli and Cardillo, 1984; Tojo and Fernández, 2007), hypervalent iodine reagents (Uyanik and Ishihara, 2009) or radical oxidants i.e., N-methylmorpholine-N-oxide (NMO) (Kumar et al, 2007; Gunasekaran et al, 2011; Saleem et al, 2013), 2,2,6,6-tetramethyl-1-piperidinyloxyl (TEMPO) (Dijksman et al, 2001; Wang et al, 2008; Allen et al, 2013) Such reactions often result in the generation of numerous wastes which caused serious environment problems. Great efforts have been devoted to the development of atom-economic and green methods.
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