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Quantum Chemical Calculations with the Inclusion of Nonspecific and Specific Solvation: Asymmetric Transfer Hydrogenation with Bifunctional Ruthenium Catalysts

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Department of Applied Chemistry, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8552, Japan
[email protected]
Cite this: J. Am. Chem. Soc. 2013, 135, 7, 2604–2619
Publication Date (Web):January 21, 2013
https://doi.org/10.1021/ja3097674
Copyright © 2013 American Chemical Society
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    Abstract

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    Details of the mechanism of asymmetric transfer hydrogenation of ketones catalyzed by two chiral bifunctional ruthenium complexes, (S)-RuH[(R,R)-OCH(Ph)CH(Ph)NH2](η6-benzene) (Ru-1) or (S)-RuH[(R,R)-p-TsNCH(Ph)CH(Ph)NH2](η6-mesitylene) (Ru-2), were studied computationally by density functional theory, accounting for the solvation effects by using continuum, discrete, and mixed continuum/discrete solvation models via “solvated supermolecules” approach. In contrast to gas phase quantum chemical calculations, where the reactions were found to proceed via a concerted three-bond asynchronous process through a six-membered pericyclic transition state, incorporation of the implicit and/or explicit solvation into the calculations suggests that the same reactions proceed via two steps in solution: (i) enantio-determining hydride transfer and (ii) proton transfer through the contact ion-pair intermediate, stabilized primarily by ionic hydrogen bonding between the cation and the anion. The calculations suggest that the proton source for neutralizing the chiral RO– anion may be either the amine group of the cationic Ru complex or, more likely, a protic solvent molecule. In the latter case, the reaction may not necessarily proceed via the 16e amido complex Ru[(R,R)-XCH(Ph)CH(Ph)NH](η6-arene). The origin of enantioselectivity is discussed in terms of the newly formulated mechanism.

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    Cartesian coordinates for all optimized compounds, tables of energy data, complete ref 37, and other details. This material is available free of charge via the Internet at http://pubs.acs.org.

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