10.1002/anie.202001704
Angewandte Chemie International Edition
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Easily accessible Cr complex catalyse the alkylation of amines by alcohols, a sustainable or green C-N formation reaction following
the borrowing hydrogen or hydrogen autotransfer concept. The work indicates that Cr complexes can mediate (de)hydrogenation
catalysis.
1 H. Schiff, Justus Liebigs Ann. Chem.1864, 131, 118–119.
2 Alcohols can be synthesized from abundantly available and indigestible biomass via pyrolysis and hydrogenation: T. P. Vispute, H. Zhang,
A. Sanna, R. Xiao, G. W. Huber, Science 2010, 330, 1222–1227.
3 A) M. H. S. A. Hamid, P. A. Slatford, J. M. J. Williams, Adv. Synth. Catal. 2007, 349, 1555–1575; b) C. Gunanathan, D. Milstein, Science
2013, 341, 1229712–1229712; c) A. Corma, J. Navas, M. J. Sabater, Chem. Rev. 2018, 118, 1410–1459; d) B. G. Reed-Berendt, K.
Polidano, L. C. Morrill, Org. Biomol. Chem. 2019, 17, 1595–1607.
4 C. F. Winans, H. Adkins, J. Am. Chem. Soc. 1932, 54, 306–312.
5 R. Grigg, T. R. B. Mitchell, S. Sutthivaiyakit, N. Tongpenyai, J. Chem. Soc., Chem. Commun. 1981, 611-612.
6 Y. Watanabe, Y. Tsuji, Y. Ohsugi, Tetrahedron Lett. 1981, 22, 2667–2670.
7 T. Irrgang, R. Kempe, Chem. Rev. 2019, 119, 2524–2549.
8 a) T. Yan, B. L. Feringa, K. Barta, Nat. Commun. 2014, 5, 5602; for important contributions of others using (derivatives of) Knölkers iron
complex see: b) H.-J. Pan, T. W. Ng, Y. Zhao, Chem. Commun. 2015, 51, 11907–11910; c) A. J. Rawlings, L. J. Diorazio, M. Wills, Org. Lett.
2015, 17, 1086–1089; d) T. Yan, B. L. Feringa, K. Barta, ACS Catal. 2016, 6, 381–388; e) B. Emayavaramban, M. Roy, B. Sundararaju,
Chem. Eur. J. 2016, 22, 3952–3955; f) T. J. Brown, M. Cumbes, L. J. Diorazio, G. J. Clarkson, M. Wills, J. Org. Chem. 2017, 82, 10489–
10503; g) K. Polidano, B. D. W. Allen, J. M. J. Williams, L. C. Morrill, ACS Catal. 2018, 8, 6440–6445. Important contributions using other iron
complexes: h) M. Bala, P. K. Verma, U. Sharma, N. Kumar, B. Singh, Green Chem. 2013, 15, 1687; i) M. Mastalir, M. Glatz, N. Gorgas, B.
Stöger, E. Pittenauer, G. Allmaier, L. F. Veiros, K. Kirchner, Chem. Eur. J. 2016, 22, 12316–12320; k) M. Mastalir, B. Stöger, E. Pittenauer,
M. Puchberger, G. Allmaier, K. Kirchner, Adv. Synth. Catal. 2016, 358, 3824–3831; m) N. Hofmann, K. C. Hultzsch, European J. Org. Chem.
2019, 2019, 3105–3111.
9 S. Rösler, M. Ertl, T. Irrgang, R. Kempe, Angew. Chem. Int. Ed. 2015, 54, 15046–15050; Angew. Chem. 2015, 127, 15260–15264; for
important contributions of others see: b) G. Zhang, Z. Yin, S. Zheng, Org. Lett. 2016, 18, 300–303; c) M. Mastalir, G. Tomsu, E. Pittenauer, G.
Allmaier, K. Kirchner, Org. Lett. 2016, 18, 3462–3465, d) S. P. Midya, J. Pitchaimani, V. G. Landge, V. Madhu, E. Balaraman, Catal. Sci.
Technol. 2018, 8, 3469–3473; e)B. Emayavaramban, P. Chakraborty, E. Manoury, R. Poli, B. Sundararaju, Org. Chem. Front. 2019, 6, 852–
857.
10 S. Elangovan, J. Neumann, J.-B. Sortais, K. Junge, C. Darcel, M. Beller, Nat. Commun. 2016, 7, 12641; for important contributions of
others see: b) J. Neumann, S. Elangovan, A. Spannenberg, K. Junge, M. Beller, Chem. Eur. J. 2017, 23, 5410–5413; c) A. Bruneau-Voisine,
D. Wang, V. Dorcet, T. Roisnel, C. Darcel, J.-B. Sortais, J. Catal. 2017, 347, 57–62; d) U. K. Das, Y. Ben-David, Y. Diskin-Posner, D. Milstein,
Angew. Chem. Int. Ed. 2018, 57, 2179–2182; e) R. Fertig, T. Irrgang, F. Freitag, J. Zander, R. Kempe, ACS Catal. 2018, 8, 8525–8530; f) K.
Das, A. Mondal, D. Srimani, J. Org. Chem. 2018, 83, 9553–9560; g) L. Homberg, A. Roller, K. C. Hultzsch, Org. Lett. 2019, 21, 3142–3147; h)
K. Das, A. Mondal, D. Pal, H. K. Srivastava, D. Srimani, Organometallics 2019, 38, 1815–1825; i) B. G. Reed-Berendt, L. C. Morrill, J. Org.
Chem. 2019, 84, 3715–3724; M. Huang, Y. Li, Y. Li, J. Liu, S. Shu, Y. Liu, Z. Ke, Chem. Commun. 2019, 55, 6213–6216.
11 a) G. A. Filonenko, R. van Putten, E. J. M. Hensen, E. A. Pidko, Chem. Soc. Rev. 2018, 47, 1459-1483; b) F. Kallmeier, R. Kempe, Angew.
Chem. Int. Ed. 2018, 57, 46-60.
12 M. Mastalir, M. Glatz, B. Stöger, M. Weil, E. Pittenauer, G. Allmaier, K. Kirchner, Inorg. Chim. Acta 2017, 455, 707–714.
13 N. Deibl, R. Kempe, Angew. Chem. Int. Ed. 2017, 56, 1663–1666; Angew. Chem. 2017, 129, 1685–1688; M. Mastalir, M. Glatz, E.
Pittenauer, G. Allmaier, K. Kirchner, J. Am. Chem. Soc. 2016, 138, 15543–15546.
14 F. Freitag, T. Irrgang, R. Kempe, J. Am. Chem. Soc. 2019, 141, 11677–11685.
6
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