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Issue 15, 2010
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Highly efficient and enantioselective hydrogenation of quinolines and pyridines with Ir-Difluorphos catalyst

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Abstract

The combination of the readily available chiral bisphosphine ligand Difluorphos with [Ir(COD)Cl]2 in THF resulted in a highly efficient catalyst system for asymmetric hydrogenation of quinolines at quite low catalyst loadings (0.05–0.002 mol%), affording the corresponding products with high enantioselectivities (up to 96%), excellent catalytic activities (TOF up to 3510 h−1) and productivities (TON up to 43000). The same catalyst was also successfully applied to the asymmetric hydrogenation of trisubstituted pyridines with nearly quantitative yields and up to 98% ee. In these two reactions, the addition of I2 additive is indispensable; but the amount of I2 has a different effect on catalytic performance.

Graphical abstract: Highly efficient and enantioselective hydrogenation of quinolines and pyridines with Ir-Difluorphos catalyst

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Publication details

The article was received on 11 Feb 2010, accepted on 18 May 2010 and first published on 07 Jun 2010


Article type: Paper
DOI: 10.1039/C002668A
Citation: Org. Biomol. Chem., 2010,8, 3464-3471
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    Highly efficient and enantioselective hydrogenation of quinolines and pyridines with Ir-Difluorphos catalyst

    W. Tang, Y. Sun, Lijin Xu, T. Wang, Qinghua Fan, K. Lam and A. S. C. Chan, Org. Biomol. Chem., 2010, 8, 3464
    DOI: 10.1039/C002668A

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