10.1002/anie.201900233
Angewandte Chemie International Edition
COMMUNICATION
Garg, Org. Lett. 2017, 19, 1910. With Cu: j) S. Das, B. Join, K. Junge,
M. Beller, Chem. Commun. 2012, 48, 2683. With Zn: k) O. O.
Kovalenko, A. Volkov, H. Adolfsson, Org. Lett. 2015, 17, 446; l) A.
Volkov, F. Tinnis, T. Slagbrand, I. Pershagen, H. Adolfsson, Chem.
Commun. 2014, 50, 14508; m) S. Das, D. Addis, S. Zhou, K. Junge, M.
Beller, J. Am. Chem. Soc. 2010, 132, 1770.
[13] With KH, see: J. P. Barham, S. E. Dalton, M. Allison, G. Nocera, A.
Young, M. P. John, T. McGuire, S. Campos. T. Tuttle, J. A. Murphy, J.
Am. Chem. Soc. 2018, 140, 11510.
[14] G. H. Chan, D. Y. Ong, Z. Yen, S. Chiba, Helv. Chim. Acta 2018, 101,
e1800049.
[15] Z. Hong, D. Y. Ong, S. K. Muduli, P. C. Too, G. H. Chan, Y. L. Tnay, S.
Chiba, Y. Nishiyama, H. Hirao, H. S. Soo, Chem. Eur. J. 2016, 22, 7108.
[16] A.-K. Wiegand, A. Rit, J. Okuda, Coord. Chem. Rev. 2016, 314, 71.
[17] T. Ohkuma, S. Hashiguchi, R. Noyori, J. Org. Chem. 1994, 59, 217.
[18] M. Uchiyama, S. Furumoto, M. Saito, Y. Kondo, T. Sakamoto, J. Am.
Chem. Soc. 1997, 119, 11425.
[7]
a) A. Chardon, T. Mohy El Dine, R. Legay, M. De Paolis, J. Rouden, J.
Blanchet, Chem. Eur. J. 2017, 23, 2005; b) D. Mukherjee, S. Shirase, K.
Mashima, J. Okuda, Angew. Chem. Int. Ed. 2016, 55, 13326; Angew.
Chem. 2016, 128, 13520; c) E. Blondiaux, T. Cantat, Chem. Commun.
2014, 50, 9349; d) R. C. Chadwick, V. Kardelis, P. Lim, A. Adronov, J.
Org. Chem. 2014, 79, 7728; e) Y. Li, J. A. Molina de La Torre, K.
Grabow, U. Bentrup, K. Junge, S. Zhou, A. Brückner, M. Beller, Angew.
Chem. Int. Ed. 2013, 52, 11577; Angew. Chem. 2013, 125, 11791.
a) P. Q. Huang, Q.-W. Lang, Y.-R. Wang, J. Org. Chem. 2016, 81,
4235; b) G. Pelletier, W. S. Bechara, A. B. Charette, J. Am. Chem. Soc.
2010, 132, 12817. With Hantzsch’s ester: c) G. Barbe, A. B. Charette,
J. Am. Chem. Soc. 2008, 130, 18.
[19] J. J. Watkins, E. C. Ashby, Inorg. Chem. 1974, 13, 2350.
[20] A. G. Myers, B. H. Yang, H. Chen, L. McKinstry, D. J. Kopecky, J. L.
Gleason, J. Am. Chem. Soc. 1997, 119, 6496.
[8]
[9]
[21] For materials characterization by powder XRD, elementary analysis,
and inductively coupled plasma-optical emission spectrometry (ICP-
OES), see the SI.
[22] H. Jenkner, US Patent US3116112A, 1953.
For hydrogenation catalyzed by frustrated Lewis pair, see: N. A. Sitte,
M. Bursch, Stefan Grimme, J. Paradies, J. Am. Chem. Soc. 2019, 141,
159.
[23] a) A. Rit, A.-K. Wiegand, D. Mukherjee, T. P. Spaniol, J. Okuda, Eur. J.
Inorg. Chem. 2018, 1114; b) P. A. Lummis, M. R. Momeni, M. W. Lui, R.
McDonald, M. J. Ferguson, M. Miskolzie, A. Brown, E. Rivard, Angew.
Chem. Int. Ed. 2014, 53, 9347; Angew. Chem. 2014, 126, 9501; c) E. C.
Ashby, A. B. Goel, Inorg. Chem. 1981, 20, 1096.
[10] a) B. Zhang, H. Li, Y. Ding, Y. Yan, J. An, J. Org. Chem. 2018, 83,
6006; b) S. R. Huq, S. Shi, R. Diao, M. Szostak, J. Org. Chem. 2017,
82, 6528; c) M. Szostak, M. Spain, A. J. Eberhart, D. J. Procter, J. Am.
Chem. Soc. 2014, 136, 2268.
[24] The DFT calculation at the M06-2X/cc-pVTZ (scrf = smd, THF) level of
theory indicated that the bridging hydride species is less stable than the
terminal hydride 5. In addition, the amide reduction with this species
was found to proceed slower; see the SI.
[11] a) P. C. Too, G. H. Chan, Y. L. Tnay, H. Hirao, S. Chiba, Angew. Chem.
Int. Ed. 2016, 55, 3719; Angew. Chem. 2016, 128, 3783; b) G. H. Chan.
D. Y. Ong, S. Chiba, Org. Synth. 2018, 95, 240.
[25] The calculations for the reduction with the monomeric ZnH2 or ZnHCl
species resulted in higher activation barrier: see the SI.
[12] D. Y. Ong, C. Tejo, K. Xu, H. Hirao, S. Chiba, Angew. Chem. Int. Ed.
2017, 56, 1840; Angew. Chem. 2017, 129, 1866.
This article is protected by copyright. All rights reserved.