Catalytic ability of a cationic Ru(II) monochloro complex for the asymmetric hydrogenation of dimethyl itaconate and enamides

Inorganic Chemistry
Isabel SerranoJordi Benet-Buchholz

Abstract

The synthesis of two Ru chloro complexes, Ru(III)Cl(3)(bpea), 1, and cis-fac-Delta-[Ru(II)Cl{(R)-(bpea)}{(S)-(BINAP)}](BF(4)), cis-fac-Delta-(R)-(S)-2, (bpea = N,N-bis(2-pyridylmethyl)ethylamine; (S)-BINAP = 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl), is described. Complex 2 is characterized in solution through UV-vis, cyclic voltammetry (CV), and 1D and 2D NMR spectroscopy. X-ray diffraction analysis indicates that in the solid state it possesses the same structure as in solution, as expected for a low-spin d(6) Ru(II)-type complex. The molecular structure of cis-fac-Delta-(R)-(S)-2, consists of a nonsymmetric complex, where the Ru metal center has a significantly distorted octahedral-type coordination because of the bulkiness of the (S)-BINAP ligand. cis-fac-Delta-(R)-(S)-2 has a remarkable catalytic performance at P = 6.8 atm of H2 and T = 70 degrees C toward the hydrogenation of prochiral double bonds both from efficiency and from stereoselectivity viewpoints. As an example, prochiral olefins of technological interest such as dimethyl itaconate, methyl 2-acetamidoacrylate or methyl 2-acetamidocinnamate are catalytically hydrogenated by cis-fac-Delta-(R)-(S)-2, with conversions higher than 99.9% and ee > 99. Furthermore, c...Continue Reading

References

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Jun 24, 2004·Journal of the American Chemical Society·Cristina SensJordi Benet-Buchholz

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Citations

Sep 24, 2015·Acta Crystallographica. Section E, Crystallographic Communications·Kasey TrotterElliott Hulley
Mar 9, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·Joaquim MolaAntoni Llobet
Nov 16, 2007·Inorganic Chemistry·Joaquim MolaAntoni Llobet

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