Full Papers
[7] a) H. Göksu, S. F. Ho, Ö. Metin, K. Korkmaz, A. Mendoza-García, M. S.
Gültekin, S. Sun, ACS Catal. 2014, 4, 1777–1782; b) L. Liu, Y. Liu, Y. Ai, J.
Li, J. Zhou, Z. Fan, H. Bao, R. Jiang, Z. Hu, J. Wang, K. Jing, Y. Wang, Q.
Liang, H. Sun, iScience 2018, 8, 61–73.
0.72:0.28. Crystallographic data have been deposited at the Cam-
bridge Crystallographic Data Center as supplementary material
number CCDC 1937366. Copies of the data can be obtained free of
charge on application to CCDC, 12 Union Road, Cambridge CB2
1EZ, UK. E-mail:deposit@ccdc.cam.ac.uk.
1
2
3
4
5
6
7
8
9
[8] J. Long, K. Shen, ACS Catal. 2017, 7, 275–284.
[9] a) S. Werkmeister, C. Bornschein, K. Junge, M. Beller, Chem. Eur. J. 2013,
19, 4437–4440; b) S. Werkmeister, C. Bornschein, K. Junge, M. Beller, Eur.
J. Org. Chem. 2013, 3671–3674.
[10] Z. Shao, S. Fu, M. Wei, Z. Zhou, Q. Liu, Angew. Chem. Int. Ed. 2016, 55,
14653–14657; Angew. Chem. 2016, 128, 14873–14877.
[11] a) V. H. Mai, G. I. Nikonov, Organometallics 2016, 35, 943–949; b) I. D.
Alshakova, B. Gabidullin, G. I. Nikonov, ChemCatChem. 2018, 10, 4860–
4869; c) V. H. Mai, S. H. Lee, G. I. Nikonov, ChemistrySelect 2017, 2, 7751–
7757.
[12] a) D. A. Valyaev, G. Lavigne, N. Lugan, Coord. Chem. Rev. 2016, 308, 191–
235; b) J. R. Carney, B. R. Dillon, S. P. Thomas, Eur. J. Org. Chem. 2016,
3912–3929; c) W. Liu, L. Ackermann, ACS Catal. 2016, 6, 3743–3752; d) B.
Maji, M. K. Barman, Synthesis 2017,49, 3377–3393; e) M. Garbe, K. Junge,
M. Beller, Eur. J. Org. Chem. 2017, 4344–4362; f) F. Kallmeier, R. Kempe,
Angew. Chem. Int. Ed. 2018, 57, 46–60; Angew. Chem. 2018, 130, 48–63;
g) N. Gorgas, K. Kirchner, Acc. Chem. Res. 2018, 51, 1558–1569; h) A.
Mukherjee, D. Milstein, ACS Catal. 2018, 8, 11435–11469; i) G. A.
Filonenko, R. van Putten, E. J. Hensen, E. A. Pidko, Chem. Soc. Rev. 2018,
47, 1459–1483; j) Y. Hu, B. Zhou, C. Wang, Acc. Chem. Res. 2018, 51, 816–
827; k) S. Waiba, M. K. Barman, B. Maji, Synlett 2019, 30, 12–20.
[13] A. Brzozowska, L. M. Azofra, V. Zubar, I. Atodiresei, L. Cavallo, M.
Rueping, O. El-Sepelgy, ACS Catal. 2018, 8, 4103–4109.
[14] K. Z. Demmans, M. E. Olson, R. H. Morris, Organometallics 2018, 37,
4608–4618.
[15] a) J. Schneekönig, K. Junge, M. Beller, Synlett 2019, 30, 503–507; b) N. V.
Shvydkiy, O. Vyhivskyi, Y. V. Nelyubina, D. S. Perekalin, ChemCatChem
2019, 11, 1602–1605.
[16] a) A. Bruneau-Voisine, D. Wang, V. Dorcet, T. Roisnel, C. Darcel, J.-B.
Sortais, Org. Lett. 2017, 19, 3656–3659; b) O. Ferraté-Martínez, C. Werlé,
G. Franciò, W. Leitner, ChemCatChem 2018, 10, 4514–4518; c) K. Ganguli,
S. Shee, D. Panja, S. Kundu, Dalton. Trans. DOI 10.1039/c8dt05001e;
d) A. Dubey, S. M. W. Rahaman, R. R. Fayzullin, J. R. Khusnutdinova,
ChemCatChem DOI 10.1002/cctc.201900358.
Supporting Information
Featuring crystallographic data for complex Mn-1 and detailed
multinuclear NMR spectra for the synthesized compounds and
for the monitoring of reactions described in the main text. Also
includes GC traces for catalytic reactions, and mass spectra for
imines detected in the crudes of reaction, and for isolated
amine hydrochlorides.
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
Acknowledgements
We thank CONACyT (A1-S-7657) and DGAPA-UNAM (IN-200119)
for their financial support. J. A. G. also thanks CONACyT for a
Ph.D. studies grant (335811). We thank Dr. Alma Arévalo for her
technical assistance.
Conflict of Interest
The authors declare no conflict of interest.
[17] D. Wei, A. Bruneau-Voisine, M. Dubois, S. Bastin, J.-B. Sortais,
ChemCatChem DOI 10.1002/cctc.201900314.
Keywords: Amines · catalysis · manganese · nitriles · transfer
hydrogenation
[18] J. A. Garduño, J. J. García, ACS Catal. 2019, 9, 392–401.
[19] S. Weber, B. Stöger, K. Kirchner, Org. Lett. 2018, 20, 7212–7215.
[20] J. A. Garduño, A. Arévalo, M. Flores-Alamo, J. J. García, Catal. Sci. Technol.
2018, 8, 2606–2616.
[21] R. Van Putten, E. A. Uslamin, M. Garbe, C. Liu, A. Gonzalez-de-Castro, M.
Lutz, K. Junge, E. J. M. Hensen, M. Beller, L. Lefort, E. A. Pidko, Angew.
Chem. Int. Ed. 2017, 56, 7531–7534; Angew. Chem. 2017, 129, 7639–
7642.
[22] S. Gomez, J. A. Peters, T. Maschmeyer, Adv. Synth. Catal. 2002, 344,
1037–1057.
[23] Compare data with Ref. 18.
[24] F. G. N. Cloke, V. C. Gibson, M. L. H. Green, V. S. B. Mtetwa, K. Prout, J.
Chem. Soc. Dalton Trans. 1988, 2227–2229.
[25] a) Agilent CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton,
England, 2013; b) R. C. Clark, J. S. Reid, Acta Crystallogr. 1995, A51, 887–
897; c) G. M. Sheldrick, Acta Cryst. 2015, A71, 3–8; d) G. M. Sheldrick,
Acta Crystallogr. 2015, C71, 3–8; e) L. J. Farrugia, J. Appl. Crystallogr.
1999, 32, 837–838.
[1] a) S. Gomez, J. A. Peters, T. Maschmeyer, Adv. Synth. Catal. 2002, 344,
1037–1057; b) H.-U. Blaser, C. Malan, B. Pugin, F. Spindler, H. Steiner, M.
Studer, Adv. Synth. Catal. 2003, 345, 103–151; c) S. Werkmeister, K.
Junge, M. Beller, Org. Process Res. Dev. 2014, 18, 289–302; d) D. B. Bagal,
B. M. Bhanage, Adv. Synth. Catal. 2015, 357, 883–900.
[2] a) D. Wang, D. Astruc, Chem. Rev. 2015, 115, 6621–6686; b) P. Häus-
singer, R. Lohmüller, A. M. Watson, Hydrogen 2. Production. Ullmann’s
Encyclopedia of Industrial Chemistry; Wiley-VCH: Weinheim, Germany.,
2011; DOI: 10.1002/14356007.o13_o03
[3] a) P. Roose, K. Eller, E. Henkes, R. Rossbacher, H. Höke. Amines, Aliphatic.
Ullmann’s Encyclopedia of Industrial Chemistry; Wiley-VCH: Weinheim,
Germany, 2015; DOI: 10.1002/14356007.a02_001.pub2; b) L. Heuer.
Benzylamine. Ullmann’s Encyclopedia of Industrial Chemistry; Wiley-
VCH: Weinheim, Germany, 2006; DOI: 10.1002/14356007.a04_009.pub2.
[4] G. R. Brown, A. J. Foubister, Synthesis 1982, 12, 1036–1037.
[5] a) R. C. Mebane, D. R. Jensen, K. R. Rickerd, B. H. Gross, Synth. Commun.
2003, 33, 3373–3379; b) X. Chen, S. Zhou, C. Qian, Arkivoc 2012, 128–
136.
[6] a) M. Vilches-Herrera, S. Werkmeister, K. Junge, A. Börner, M. Beller,
Catal. Sci. Technol. 2014, 4, 629–632; b) L. Liu, J. Li, Y. Ai, Y. Liu, J. Xiong,
H. Wang, Y. Qiao, W. Liu, S. Tan, S. Feng, K. Wang, H. Sun, Q. Liang,
Green Chem. 2019, 21, 1390–1395.
Manuscript received: June 30, 2019
Accepted manuscript online: September 10, 2019
Version of record online: ■■■, ■■■■
ChemCatChem 2019, 11, 1–9
8
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
��
These are not the final page numbers!