Manganese-Catalyzed Asymmetric Hydrogenation of Quinolines Enabled by π–π Interaction**
Chenguang Liu
Center of Basic Molecular Science (CBMS), Department of Chemistry, Tsinghua University, Beijing, 100084 China
Search for more papers by this authorMingyang Wang
Center of Basic Molecular Science (CBMS), Department of Chemistry, Tsinghua University, Beijing, 100084 China
Search for more papers by this authorShihan Liu
Chongqing Key Laboratory of Theoretical and Computational Chemistry, School of Chemistry and Chemical Engineering, Chongqing University, Chongqing, 400030 China
Search for more papers by this authorYujie Wang
Center of Basic Molecular Science (CBMS), Department of Chemistry, Tsinghua University, Beijing, 100084 China
Search for more papers by this authorYong Peng
Center of Basic Molecular Science (CBMS), Department of Chemistry, Tsinghua University, Beijing, 100084 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Yu Lan
Institute of Green Catalysis, College of Chemistry, Zhengzhou University, Zhengzhou, Henan, 450001 China
Chongqing Key Laboratory of Theoretical and Computational Chemistry, School of Chemistry and Chemical Engineering, Chongqing University, Chongqing, 400030 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Qiang Liu
Center of Basic Molecular Science (CBMS), Department of Chemistry, Tsinghua University, Beijing, 100084 China
Search for more papers by this authorChenguang Liu
Center of Basic Molecular Science (CBMS), Department of Chemistry, Tsinghua University, Beijing, 100084 China
Search for more papers by this authorMingyang Wang
Center of Basic Molecular Science (CBMS), Department of Chemistry, Tsinghua University, Beijing, 100084 China
Search for more papers by this authorShihan Liu
Chongqing Key Laboratory of Theoretical and Computational Chemistry, School of Chemistry and Chemical Engineering, Chongqing University, Chongqing, 400030 China
Search for more papers by this authorYujie Wang
Center of Basic Molecular Science (CBMS), Department of Chemistry, Tsinghua University, Beijing, 100084 China
Search for more papers by this authorYong Peng
Center of Basic Molecular Science (CBMS), Department of Chemistry, Tsinghua University, Beijing, 100084 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Yu Lan
Institute of Green Catalysis, College of Chemistry, Zhengzhou University, Zhengzhou, Henan, 450001 China
Chongqing Key Laboratory of Theoretical and Computational Chemistry, School of Chemistry and Chemical Engineering, Chongqing University, Chongqing, 400030 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Qiang Liu
Center of Basic Molecular Science (CBMS), Department of Chemistry, Tsinghua University, Beijing, 100084 China
Search for more papers by this authorA previous version of this manuscript has been deposited on a preprint server (https://doi.org/10.26434/chemrxiv.13034363.v2).
Graphical Abstract
The non-noble metal-catalyzed asymmetric hydrogenation of N-heteroaromatics, quinolines, has been realized by using a well-defined chiral pincer manganese catalyst, with up to 97 % ee and 3840 TON.
Abstract
The non-noble metal-catalyzed asymmetric hydrogenation of N-heteroaromatics, quinolines, is reported. A new chiral pincer manganese catalyst showed outstanding catalytic activity in the asymmetric hydrogenation of quinolines, affording high yields and enantioselectivities (up to 97 % ee). A turnover number of 3840 was reached at a low catalyst loading (S/C=4000), which is competitive with the activity of most effective noble metal catalysts for this reaction. The precise regulation of the enantioselectivity were ensured by a π–π interaction.
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