Citation: Wang Zelong, Chen Lei, Mao Guoliang, Wang Congyang. Simple manganese carbonyl catalyzed hydrogenation of quinolines and imines[J]. Chinese Chemical Letters, ;2020, 31(7): 1890-1894. doi: 10.1016/j.cclet.2020.02.025 shu

Simple manganese carbonyl catalyzed hydrogenation of quinolines and imines

Wang Zelong ^a,b ,
Chen Lei ^a,c ,
Mao Guoliang ^c,**, ,
Wang Congyang ^a,b,d,*,

a.
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, CAS Research/Education Center for Excellence in Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
b.
University of Chinese Academy of Sciences, Beijing 100049, China
c.
Provincial Key Laboratory of Oil & Gas Chemical Technology, College of Chemistry and Chemical Engineering, Northeast Petroleum University, Daqing 163318, China
d.
Physical Science Laboratory, Huairou National Comprehensive Science Center, Beijing 101400, China

^**

maoguoliang@nepu.edu.cn

wangcy@iccas.ac.cn

Received Date: 13 January 2020
Revised Date: 11 February 2020
Accepted Date: 13 February 2020
Available Online: 14 February 2020

Figures(6)

Manganese-catalyzed hydrogenation of unsaturated molecules has made tremendous progresses recently benefiting from non-innocent pincer or bidentate ligands for manganese. Herein, we describe the hydrogenation of quinolines and imines catalyzed by simple manganese carbonyls, Mn₂(CO)₁₀ or MnBr(CO)₅, thus eliminating the prerequisite pincer-type or bidentate ligands.
- Manganese,
- Hydrogenation,
- Quinolines,
- Imines,
- Homogeneous catalysis
1. [1]
  De Vries J.G., Elsevier C.J.. The Handbook of Homogeneous Hydrogenation[J]. Wiley-VCH.Weinheim, 2007.
2. [2]
  (a) R. Noyori, T. Ohkuma, Angew. Chem. Int. Ed. 40 (2001) 40-73;
  (b) J.H. Xie, S.F. Zhu, Q.L. Zhou, Chem. Rev. 111 (2011) 1713-1760;
  (c) B. Zhao, Z. Han, K. Ding, Angew. Chem. Int. Ed. 52 (2013) 4744-4788;
  (d) Y.M. He, Y. Feng, Q.H. Fan, Acc. Chem. Res. 47 (2014) 2894-2906;
  (e) D.S. Wang, Q.A. Chen, S.M. Lu, Y.G. Zhou, Chem. Rev. 112 (2012) 2557-2590;
  (f) W. Tang, X. Zhang, Chem. Rev. 103 (2003) 3029-3069.
3. [3]
  (a) Z. Zhang, N.A. Butt, M. Zhou, D. Liu, W. Zhang, Chin. J. Chem. 36 (2018) 443-454;
  (b) G.A. Filonenko, R. van Putten, E.J.M. Hensen, E.A. Pidko, Chem. Soc. Rev. 47 (2018) 1459-1483;
  (c) W. Liu, B. Sahoo, K. Junge, M. Beller, Acc. Chem. Res. 51 (2018) 1858-1869;
  (d) W. Ai, R. Zhong, X. Liu, Q. Liu, Chem. Rev. 119 (2019) 2876-2953;
  (e) T. Irrgang, R. Kempe, Chem. Rev. 119 (2019) 2524-2549;
  (f) L. Alig, M. Fritz, S. Schneider, Chem. Rev. 119 (2019) 2681-2751.
4. [4]
  (a) D.A. Valyaev, G. Lavigne, N. Lugan, Coord. Chem. Rev. 308 (2016) 191-235;
  (b) W. Liu, L. Ackermann, ACS Catal. 6 (2016) 3743-3752;
  (c) J.R. Carney, B.R. Dillon, S.P. Thomas, Eur. J. Org. Chem. 2016 (2016) 3912-3929;
  (d) M. Garbe, K. Junge, M. Beller, Eur. J. Org. Chem. 30 (2017) 4344-4362;
  (e) R.J. Trovitch, Acc. Chem. Res. 50 (2017) 2842-2852;
  (f) A. Mukherjee, D. Milstein, ACS Catal. 8 (2018) 11435-11469;
  (g) Y. Hu, B. Zhou, C. Wang, Acc. Chem. Res. 51 (2018) 816-827;
  (h) X. Yang, C. Wang, Chem. Asian J. 13 (2018) 2307-2315.
5. [5]
  (a) B. Maji, M. Barman, Synthesis 49 (2017) 3377-3393;
  (b) F. Kallmeier, R. Kempe, Angew. Chem. Int. Ed. 57 (2018) 46-60;
  (c) N. Gorgas, K. Kirchner, Acc. Chem. Res. 51 (2018) 1558-1569.
6. [6]
  (a) S. Elangovan, C. Topf, S. Fischer, et al., J. Am. Chem. Soc. 138 (2016) 8809-8814;
  (b) F. Kallmeier, T. Irrgang, T. Dietel, R. Kempe, Angew. Chem. Int. Ed. 55 (2016) 11806-11809;
  (c) A. Bruneau-Voisine, D. Wang, T. Roisnel, C. Darcel, J.B. Sortais, Catal. Commun. 92 (2017) 1-4;
  (d) D. Wei, A. Bruneau-Voisine, T. Chauvin, et al., Adv. Synth. Catal. 360 (2018) 676-681;
  (e) S. Weber, B. Stoeger, K. Kirchner, Org. Lett. 20 (2018) 7212-7215;
  (f) M. Glatz, B. Stoger, D. Himmelbauer, L.F. Veiros, K. Kirchner, ACS Catal. 8 (2018) 4009-4016.
7. [7]
  (a) M.B. Widegren, G.J. Harkness, A.M. Slawin, D.B. Cordes, M.L. Clarke, Angew. Chem. Int. Ed. 56 (2017) 5825-5828;
  (b) M. Garbe, K. Junge, S. Walker, et al., Angew. Chem. Int. Ed. 56 (2017) 11237-11241;
  (c) M. Garbe, Z. Wei, B. Tannert, et al., Adv. Synth. Catal. 361 (2019) 1913-1920;
  (d)L.Zhang, Y.Tang, Z.Han, K.Ding, Angew.Chem.Int.Ed.58 (2019)4973-4977;
  (e) F. Ling, H. Hou, J. Chen, et al., Org. Lett. 21 (2019) 3937-3941.
8. [8]
  J.A. Garduno, J.J. García, ACS Catal. 9 (2019) 392-401. doi: 10.1021/acscatal.8b03899
9. [9]
  (a) A. Dubey, L. Nencini, R.R. Fayzullin, C. Nervi, J.R. Khusnutdinova, ACS Catal. 7 (2017) 3864-3868;
  (b) F. Bertini, M. Glatz, N. Gorgas, et al., Chem. Sci. 8 (2017) 5024-5029;
  (c) S. Kar, A. Goeppert, J. Kothandaraman, G.K.S. Prakash, ACS Catal. 7 2017) 6347-6351.
10. [10]
  (a) A. Kumar, T. Janes, N.A. Espinosa-Jalapa, D. Milstein, Angew. Chem. Int. Ed. 57 (2018) 12076-12080;
  (b) V. Zubar, Y. Lebedev, L.M. Azofra, et al., Angew. Chem. Int. Ed. 57 (2018) 13439-13443;
  (c) A. Kaithal, M. Hoelscher, W. Leitner, Angew. Chem. Int. Ed. 57 (2018) 13449-13453.
11. [11]
  (a) V.Papa, J.R.Cabrero-Antonino, E.Alberico, etal., Chem.Sci.8 (2017) 3576-3585;
  (b) Y.Q. Zou, S. Chakraborty, A. Nerush, et al., ACS Catal. 8 (2018) 8014-8019.
12. [12]
  (a) S. Elangovan, M. Garbe, H. Jiao, et al., Angew. Chem. Int. Ed. 55 (2016) 15364-15368;
  (b) R. van Putten, E.A. Uslamin, M. Garbe, et al., Angew. Chem. Int. Ed. 56 (2017) 7531-7534;
  (c) N.A. Espinosa-Jalapa, A. Nerush, L.J. Shimon, et al., Chem. Eur. J. 23 (2017) 5934-5938;
  (d) M.B. Widegren, M.L. Clarke, Org. Lett. 20 (2018) 2654-2658.
13. [13]
  U.K. Das, A. Kumar, Y. Ben-David, M.A. Iron, D. Milstein, J. Am. Chem. Soc. 141 (2019) 12962-12966. doi: 10.1021/jacs.9b05591
14. [14]
  (a) D. Wei, A. Bruneau-Voisine, D.A. Valyaev, N. Lugan, J.B. Sortais, Chem. Commun. 54 (2018) 4302-4305;
  (b) F. Freitag, T. Irrgang, R. Kempe, J. Am. Chem. Soc. 141 (2019) 11677-11685;
  (c) Y. Wang, L. Zhu, Z. Shao, et al., J. Am. Chem. Soc. 141 (2019) 17337-17349.
15. [15]
  (a) R. He, Z.T. Huang, Q.Y. Zheng, C. Wang, Angew. Chem. Int. Ed. 53 (2014) 4950-4953;
  (b) X. Yang, C. Wang, Angew. Chem. Int. Ed. 57 (2018) 923-928;
  (c) X. Yang, C. Wang, Chin. J. Chem. 36 (2018) 1047-1051.
16. [16]
  V. Papa, Y. Cao, A. Spannenberg, K. Junge, M. Beller, Nat. Catal. 3 (2020) 135-142. doi: 10.1038/s41929-019-0404-6
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