10.1002/cctc.201900358
ChemCatChem
FULL PAPER
0) or transition states (NIMAG = 1) on the potential energy surface. The
IRC calculations were performed to confirm the nature of each transition
state. The solvation energies were calculated in 2-propanol (ε = 19.26)
using CPCM model.[27] Important bond parameters for the intermediates
and the transition states (TS) are provided in Figure 3. The computed
reaction profile along with calculated solvent-corrected energies (Scheme
Angew. Chem. Int. Ed. 2018, 57, 12076-12080; e) Y.-Q. Zou, S.
Chakraborty, A. Nerush, D. Oren, Y. Diskin-Posner, Y. Ben-David, D.
Milstein, ACS Catal. 2018, 8, 8014-8019; f) N. Gorgas, K. Kirchner, Acc.
Chem. Res. 2018, 51, 1558-1569; g) F. Kallmeier, R. Kempe, Angew.
Chem. Int. Ed. 2018, 57, 46-60; h) M. Garbe, K. Junge, S. Walker, Z.
Wei, H. Jiao, A. Spannenberg, S. Bachmann, M. Scalone, M. Beller,
Angew. Chem. Int. Ed. 2017, 56, 11237-11241; i) S. Elangovan, M.
Garbe, H. Jiao, A. Spannenberg, K. Junge, M. Beller, Angew. Chem. Int.
Ed. 2016, 55, 15364-15368; j) S. Kar, A. Goeppert, J. Kothandaraman,
G. K. S. Prakash, ACS Catal. 2017, 7, 6347-6351; k) S. Elangovan, C.
Topf, S. Fischer, H. Jiao, A. Spannenberg, W. Baumann, R. Ludwig, K.
Junge, M. Beller, J. Am. Chem. Soc. 2016, 138, 8809-8814; l) F.
Kallmeier, T. Irrgang, T. Dietel, R. Kempe, Angew. Chem. Int. Ed. 2016,
55, 11806-11809; m) M. B. Widegren, G. J. Harkness, A. M. Z. Slawin,
D. B. Cordes, M. L. Clarke, Angew. Chem. Int. Ed. 2017, 56, 5825-
5828; n) A. Mukherjee, D. Milstein, ACS Catal. 2018, 8, 11435-11469.
a) U. K. Das, S. Chakraborty, Y. Diskin-Posner, D. Milstein, Angew.
Chem. Int. Ed. 2018, 57, 13444-13448; b) S. Chakraborty, U. K. Das, Y.
Ben-David, D. Milstein, J. Am. Chem. Soc. 2017, 139, 11710-11713; c)
A. Nerush, M. Vogt, U. Gellrich, G. Leitus, Y. Ben-David, D. Milstein, J.
Am. Chem. Soc. 2016, 138, 6985-6997; d) A. Mukherjee, A. Nerush, G.
Leitus, L. J. W. Shimon, Y. Ben David, N. A. Espinosa Jalapa, D.
Milstein, J. Am. Chem. Soc. 2016, 138, 4298-4301; e) S. Chakraborty,
P. Daw, Y. Ben David, D. Milstein, ACS Catal. 2018, 8, 10300-10305; f)
G. Zhang, T. Irrgang, T. Dietel, F. Kallmeier, R. Kempe, Angew. Chem.
Int. Ed. 2018, 57, 9131-9135; g) A. Bruneau-Voisine, D. Wang, V.
Dorcet, T. Roisnel, C. Darcel, J.-B. Sortais, J. Catal. 2017, 347, 57-62;
h) J. Neumann, S. Elangovan, A. Spannenberg, K. Junge, M. Beller,
Chem. Eur. J. 2017, 23, 5410-5413.
3
and Supp. Info, Scheme S1 and Figures S67-S70) and atomic
coordinates are provided in the Supp. Info.
Acknowledgements
We thank Dr. Michael Roy and Dr. Yoshiteru Iinuma for HRMS
and ICP-MS analysis, respectively. We also thank Dr. Eugene
Khaskin for helpful discussions. The authors acknowledge
Okinawa Institute of Science and Technology Graduate
University for start-up funding.
[5]
† Current address: Ram Jaipal College (A Post Graduate Unit of Jai Prakash
University), Dak Bunglow Road, Saran, Chhapra, Bihar-841301, India.
Keywords: manganese • transfer hydrogenation • N-
heterocycles • non-phosphine ligands • mechanistic studies
[1]
a) R. Noyori, S. Hashiguchi, Acc. Chem. Res. 1997, 30, 97-102; b) T.
Ikariya, A. J. Blacker, Acc. Chem. Res. 2007, 40, 1300-1308; c) X. Wu,
J. Xiao, Chem. Commun. 2007, 2449-2466; d) D. Wang, D. Astruc,
Chem. Rev. 2015, 115, 6621-6686; e) S. Gladiali, E. Alberico, Chem.
Soc. Rev. 2006, 35, 226-236; f) A. Robertson, T. Matsumoto, S. Ogo,
Dalton Trans. 2011, 40, 10304-10310; g) S. E. Clapham, A. Hadzovic,
R. H. Morris, Coord. Chem. Rev. 2004, 248, 2201-2237.
[6]
a) O. Martinez-Ferrate, C. Werle, G. Francio, W. Leitner,
ChemCatChem 2018, 10, 4514-4518; b) A. Zirakzadeh, S. R. M. M. de
Aguiar, B. Stoeger, M. Widhalm, K. Kirchner, ChemCatChem 2017, 9,
1744-1748; c) M. Perez, S. Elangovan, A. Spannenberg, K. Junge, M.
Beller, ChemSusChem 2017, 10, 83-86; d) D. Wang, A. Bruneau-
Voisine, J.-B. Sortais, Catal. Commun. 2018, 105, 31-36; e) A.
Bruneau-Voisine, D. Wang, V. Dorcet, T. Roisnel, C. Darcel, J.-B.
Sortais, Org. Lett. 2017, 19, 3656-3659.
[2]
[3]
a) J. Wu, F. Wang, Y. Ma, X. Cui, L. Cun, J. Zhu, J. Deng, B. Yu, Chem.
Commun. 2006, 1766-1768; b) C. M. Moore, N. K. Szymczak, Chem.
Commun. 2013, 49, 400-402; c) I. S. Sinopalnikova, T. A. Peganova, N.
V. Belkova, E. Deydier, J.-C. Daran, E. S. Shubina, A. M. Kalsin, R. Poli,
Eur. J. Inorg. Chem. 2018, 2018, 2285-2299; d) R. Malacea, R. Poli, E.
Manoury, Coord. Chem. Rev. 2010, 254, 729-752.
[7]
a) F. Chen, B. Sahoo, C. Kreyenschulte, H. Lund, M. Zeng, L. He, K.
Junge, M. Beller, Chem. Sci. 2017, 8, 6239-6246; b) Y. Han, Z. Wang,
R. Xu, W. Zhang, W. Chen, L. Zheng, J. Zhang, J. Luo, K. Wu, Y. Zhu,
C. Chen, Q. Peng, Q. Liu, P. Hu, D. Wang, Y. Li, Angew. Chem. Int. Ed.
2018, 57, 11262-11266; c) I. Sorribes, L. Liu, A. Domenech-Carbo, A.
Corma, ACS Catal. 2018, 8, 4545-4557.
a) S. Zhou, S. Fleischer, K. Junge, S. Das, D. Addis, M. Beller, Angew.
Chem. Int. Ed. 2010, 49, 8121-8125; b) S. Enthaler, B. Hagemann, G.
Erre, K. Junge, M. Beller, Chem. Asian J. 2006, 1, 598-604; c) S.
Enthaler, G. Erre, M. K. Tse, K. Junge, M. Beller, Tetrahedron Lett.
2006, 47, 8095-8099; d) G. Wienhoefer, I. Sorribes, A. Boddien, F.
Westerhaus, K. Junge, H. Junge, R. Llusar, M. Beller, J. Am. Chem.
Soc. 2011, 133, 12875-12879; e) A. A. Mikhailine, M. I. Maishan, R. H.
Morris, Org. Lett. 2012, 14, 4638-4641; f) G. Wienhoefer, F. A.
Westerhaus, K. Junge, M. Beller, J. Organomet. Chem. 2013, 744, 156-
159; g) C. Sui-Seng, F. N. Haque, A. Hadzovic, A.-M. Putz, V. Reuss, N.
Meyer, A. J. Lough, M. Zimmer-De Iuliis, R. H. Morris, Inorg. Chem.
2009, 48, 735-743; h) N. Meyer, A. J. Lough, R. H. Morris, Chem. Eur.
J. 2009, 15, 5605-5610; i) T. Hashimoto, S. Urban, R. Hoshino, Y. Ohki,
K. Tatsumi, F. Glorius, Organometallics 2012, 31, 4474-4479; j) A. A.
Mikhailine, M. I. Maishan, A. J. Lough, R. H. Morris, J. Am. Chem. Soc.
2012, 134, 12266-12280; k) P. O. Lagaditis, A. J. Lough, R. H. Morris, J.
Am. Chem. Soc. 2011, 133, 9662-9665; l) P. E. Sues, A. J. Lough, R. H.
Morris, Organometallics 2011, 30, 4418-4431.
[8]
[9]
J. R. Cabrero-Antonino, R. Adam, K. Junge, R. Jackstell, M. Beller,
Catal. Sci. Technol. 2017, 7, 1981-1985.
a) F. Glorius, Org. Biomol. Chem. 2005, 3, 4171-4175; b) Z. Yu, W. Jin,
Q. Jiang, Angew. Chem. Int. Ed. 2012, 51, 6060-6072; c) D.-S. Wang,
Q.-A. Chen, S.-M. Lu, Y.-G. Zhou, Chem. Rev. 2012, 112, 2557-2590;
d) Z.-P. Chen, Y.-G. Zhou, Synthesis 2016, 48, 1769-1781.
[10] 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) Y. Watanabe, T. Ohta, Y. Tsuji, T. Hiyoshi, Y. Tsuji, Bull.
Chem. Soc. Jpn. 1984, 57, 2440-2444; d) V. Parekh, J. A. Ramsden, M.
Wills, Tetrahedron: Asymmetry 2010, 21, 1549-1556.
[11] a) P. Frediani, L. Rosi, L. Cetarini, M. Frediani, Inorg. Chim. Acta 2006,
359, 2650-2657; b) J. Wu, C. Wang, W. Tang, A. Pettman, J. Xiao,
Chem. Eur. J. 2012, 18, 9525-9529; c) J. Wu, W. Tang, A. Pettman, J.
Xiao, Adv. Synth. Catal. 2013, 355, 35-40; d) C. Wang, B. Villa-Marcos,
J. Xiao, Chem. Commun. 2011, 47, 9773-9785; e) C. Wang, C. Li, X.
Wu, A. Pettman, J. Xiao, Angew. Chem. Int. Ed. 2009, 48, 6524-6528;
f) L. Zhang, R. Qiu, X. Xue, Y. Pan, C. Xu, H. Li, L. Xu, Adv. Synth.
Catal. 2015, 357, 3529-3537; g) K. Matsui, Y. Maegawa, M. Waki, S.
Inagaki, Y. Yamamoto, Catal. Sci. Technol. 2018, 8, 534-539.
[4]
a) T. Zell, R. Langer, ChemCatChem 2018, 10, 1930-1940; b) G. A.
Filonenko, R. van Putten, E. J. M. Hensen, E. A. Pidko, Chem. Soc.
Rev. 2018, 47, 1459-1483; c) 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; d) A. Kumar, T. Janes, N. A. Espinosa-Jalapa, D. Milstein,
[12] a) K.-i. Fujita, C. Kitatsuji, S. Furukawa, R. Yamaguchi, Tetrahedron
Lett. 2004, 45, 3215-3217; b) A. M. Voutchkova, D. Gnanamgari, C. E.
This article is protected by copyright. All rights reserved.