Issue 15, 2010
From the journal:

Organic & Biomolecular Chemistry

Highly efficient and enantioselective hydrogenation of quinolines and pyridines with Ir-Difluorphos catalyst†

Weijun Tang,a   Yawei Sun,a   Lijin Xu,*a   Tianli Wang,b   Qinghua Fan,b   Kim-Hung Lamc  and  Albert S. C. Chanc  

* Corresponding authors

a Department of Chemistry, Renmin University of China, Beijing 100872, China
E-mail: xulj@chem.ruc.edu.cn

b Beijing National Laboratory for Molecular Sciences, CAS key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China

c Department of Applied Biology & Chemical Technology and Open Laboratory of Chirotechnology of the Institute of Molecular Technology for Drug Discovery & Synthesis, The Hong Kong Polytechnic University, Hong Kong, China

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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Article information

DOI
https://doi.org/10.1039/C002668A
Article type
Paper
Submitted
11 Feb 2010
Accepted
18 May 2010
First published
07 Jun 2010

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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