Extracurricular laboratory:new discovery of (2R,3S,4R,5R)-2,3,4,5-Tetrahydroxy-6-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)hexanal

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Neutral and cationic ruthenium carbonyl complexes [Ru(CO) (2,2?-dipyridylamine)(PR3)Cl2] and [Ru(CO)(N-N)(PPh3)2(H)]Cl: Synthesis, structural characterization and transfer-hydrogenation

The neutral complexes [Ru(CO)(dpa)(PR3)Cl2] (R = Ph (1) or p-tol (2); dpa = 2,2?-dipyridylamine) were synthesized by the reaction of [Ru(CO)(dmf)(PR3)2Cl2] (dmf = N,N-dimethylformamide) and the dpa ligand, while the cationic carbonyl hydride complexes [Ru(CO) (N-N)(PPh3)2(H)]Cl were synthesized by reaction of [Ru(CO)(PPh3)3Cl(H)] and the appropriate N-N ligand [N-N = 2,2?-bipyridine = bipy (3), 2,2?-4,4?dimethyl-bipyridine = dmb (4) and 2,2?-dipyridylamine = dpa (5)]. The complexes were characterized by NMR (31P, 1H and HMBC 1H-31P), FTIR, elemental analysis and X-ray diffraction. The molecular structure of [Ru(CO)(dpa)(PPh3) Cl2] (1) was determined by X-ray crystallography. The crystal packing is stabilized by strong (CH3)O-H…Cl and N-H…OH(CH3) hydrogen bonds between symmetry-related molecules leading to the formation of dimers. Complexes 1-6 were evaluated as pre-catalysts for the reduction of acetophenone under transfer-hydrogenation conditions using isopropanol as hydrogen source, and conversions up to 86 % in 4 h were achieved.

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Reference:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics