ChemComm
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COMMUNICATION
7
8
were used as the substrates, phenanthridines 7a and 7b were
generated in yield of 55% and 59%, respectively (Scheme 7).
The yields are much higher than those obtained under the
condition of n-Bu3SnH and AIBN.7
In conclusion, we have demonstrated that the catalytic
system of FeCl2/NHC SIPrHCl (L6) can enable diphenyl tertiary
azides to be converted to imines via 1,2-phenyl migration.
One-pot reduction of the thus formed imines by NaBH4
provides aniline products in high yield. Further study is
undergoing in our lab to elucidate the mechanistic issues as
well as to exploit the catalytic capacity of FeCl2/NHC system for
other types of azide-involved amination reactions.
1607-1608.
DOI: 10.1039/D0CC04579A
(a) T. Yang, X. Fan, X. Zhao and W. Yu, Org. Lett., 2018, 20
,
1875-1879; (b) T. Yang, Y. Lin, C. Yang and W. Yu, Green
Chem., 2019, 21, 6097-6102.
9
X. Zhao, S. Liang, X. Fan, T. Yang and W. Yu, Org. Lett., 2019,
21, 1559-1563.
10 (a) M. N. Hopkinson, C. Richter, M. Schedler and F. Glorius,
Nature, 2014, 510, 485-496; (b) D. J. Nelson, Eur. J. Inorg.
Chem., 2015, 2012-2027; (c) J. Cheng, L. Wang, P. Wang and
L. Deng, Chem. Rev., 2018, 118, 9930-9987.
11 (a) M. J. Ingleson and R. A. Layfield, Chem. Commun., 2012,
48, 3579-3589; (b) D. Bézier, J. B. Sortais and C. Darcel, Adv.
Synth. Catal., 2013, 355, 19-33; (c) K. Riener, S. Haslinger, A.
Raba, M. P. Hogerl, M. Cokoja, W. A. Herrmann and F. E.
Kuhn, Chem. Rev., 2014, 114, 5215-5272.
12 (a) R. B. Bedford, M. Betham, D. W. Bruce, A. A. Danopoulos,
R. M. Frost and M. Hird, J. Org. Chem., 2006, 71, 1104-1110;
(b) T. Hatakeyama and M. Nakamura, J. Am. Chem. Soc.,
2007, 129, 9844-9845; (c) H.-h. Gao, C.-h. Yan, X.-P. Tao, Y.
Xia, H.-M. Sun,Q. Shen and Y. Zhan, Organometallics, 2010,
29, 4189-4192; (d) A. L. Silberstein, S. D. Ramgren and N. K.
Garg, Org. Lett., 2012, 14, 3796-3799.
Conflicts of interest
There are no conflicts to declare.
13 (a) R. Huang, X. Chen, C. Mou, G. Luo, Y. Li, X. Li, W. Xue, Z.
Jin and Y. R. Chi, Org. Lett., 2019, 21, 4340-4344; (b) S. Santra,
U. Maji and J. Guin, Org. Lett., 2020, 22, 468-473.
Acknowledgements
The authors thank the National Natural Science Foundation of
China (No. 21772077) and State Key Laboratory of Applied
Organic Chemistry for financial support.
14 (a) J. Louie and R. H. Grubbs, Chem. Commun., 2000, 1479-
1480; (b) G. J. P. Britovsek, S. A. Cohen, V. C. Gibson, P. J.
Maddox and M. van Meurs, Angew. Chem. Int. Ed., 2002, 41
,
489-491; (c) D. S. McGuinness, V. C. Gibson and J. W. Steed,
Organometallics, 2004, 23, 6288-6292; (d) Y. Wang, H. Sun, X.
Tao, Q. Shen and Y. Zhang, Chin. Sci. Bull., 2007, 52, 3193-
3199.
Notes and references
1
(a) A. I. O. Suarez, V. Lyaskovskyy, J. N. H. Reek, J. I. van der
Vlugt and B. de Bruin, Angew. Chem. Int. Ed., 2013, 52
15 (a) H. Zhang, Z. Ouyang, Y. Liu, Q. Zhang, L. Wang and L. Deng,
Angew. Chem. Int. Ed., 2014, 53, 8432-8436; (b) L. Wang, L.
Hu, H. Zhang, H. Chen and L. Deng, J. Am. Chem. Soc., 2015,
137, 14196-14207; (c) J. Cheng, J. Liu, X. Leng, T. Lohmiller, A.
,
12510-12529; (b) D. Intrieri, P. Zardi, A. Caselli and E. Gallo,
Chem. Commun., 2014, 50, 11440-11453; (c) K. Shin, H. Kim
and S. Chang, Acc. Chem. Res., 2015, 48, 1040-1052; (d) Y.
Park, Y. Kim and S. Chang, Chem Rev., 2017, 117, 9247-9301.
(a) L. Zhang and L. Deng, Chin. Sci. Bull., 2012, 57, 2352-2360;
(b) P. Wang and L. Deng, Chin. J. Chem., 2018, 36, 1222-1240;
Schnegg, E. Bill, S. Ye and L. Deng, Inorg. Chem., 2019, 58
7634-7644.
,
2
16 B. P. Jacobs, P. T. Wolczanski, Q. Jiang, T. R. Cundari and S. N.
MacMillan, J. Am. Chem. Soc., 2017, 139, 12145-12148.
17 (a) E. T. Hennessy and T. A. Betley, Science, 2013, 340, 591-
595; (b) D. A. Iovan, M. J.Wilding, Y. Baek, E. T. Hennessy and
T. A. Betley, Angew. Chem. Int. Ed., 2017, 56, 15599-15602.
18 (a) C. Nathan, Z. Lin, T. Zhang, J. C. Gilhula,; C. W. Abney and
W. Lin, J. Am. Chem. Soc., 2016, 138, 3501-3509; (b) N. C.
Thacker, P. Ji, Z. Lin, A. Urban and W. Lin, Faraday Discuss.,
2017, 201, 303-315.
19 (a) B. Bagh, D. L. J. Broere, V. Sinha, P. F. Kuijpers, N. P. van
Leest, B. de Bruin, S. Demeshko, M. A. Siegler and J. I. van
der Vlugt, J. Am. Chem. Soc., 2017, 139, 5117-5124; (b) P. F.
Kuijpers, M. J. Tiekink, W. B. Breukelaar, D. L. J. Broere, N. P.
van Leest, J. I. van der Vlugt, J. N. H. Reek and B. de Bruin,
Chem. Eur. J., 2017, 23, 7945-7952.
(c) B. Plietker and A. Röske, Catal. Sci. Technol., 2019, 9,
4188-4197; (d) Y. Liu, T. You, T. T. Wang and C. M. Che,
Tetrahedron, 2019, 75, 130607; (e) S. Graßl, J Singer and Paul
Knochel, Angew. Chem. Int. Ed., 2020, 59, 335-338; (f) J. Lee,
J. Lee, H. Jung, D. Kim, J. Park and S. Chang, J. Am. Chem. Soc.,
2020, 142, 12324-12332.
3
(a) C. Bolm, J. Legros, J. Le Paih and L. Zani, Chem. Rev., 2004,
104, 6217-6254; (b) Iron Catalysis in Organic Chemistry:
Reactions and Applications, B. Plietker, Ed.; Wiley-VCH:
Weinheim, Germany, 2008; (c) Top. Organomet. Chem.—
Iron Catalysis: Fundamentals and Applications, B. Plietker,
Ed.; Springer Verlag: Berlin, 2011, Vol. 33; (d) Top.
Organomet. Chem.—Iron Catalysis II, B. Plietker, Ed.;
Springer Verlag: Berlin, 2015, Vol. 50; (e) I. Bauer and H. J.
Knolker, Chem. Rev., 2015, 115, 3170-3387; (f) A. Furstner,
20 (a) K. P. Shing, Y. Liu, B. Cao, X. Y. Chang, T. You and C. M.
Che, Angew. Chem. Int. Ed., 2018, 57, 11947-11951; (b) Y. D.
ACS Cent. Sci., 2016, 2, 778-789.
Du, Z. J. Xu, C. Y. Zhou and C. M. Che, Org. Lett., 2019, 21
,
4
(a) K. Murai, T. Kobayashi, M. Miyoshi and H. Fujioka, Org.
Lett., 2018, 20, 2333-2337; (b) W. Yamakoshi, M. Arisawa
and K. Murai, Org. Lett., 2019, 21, 3023-3027.
895-899.
21 S. Liang, X. Zhao, T. Yang and W. Yu, Org. Lett., 2020, 22
,
1961-1965.
5
6
Molecular Rearrangements in Organic Synthesis, C. M. Rojas
ed., John Wiley & Sons, 2015.
(a) R. A. Abramovitch and E. P. Kyba, J. Am. Chem. Soc., 1974,
96, 480-488; (b) E. P. Kyba and R. A. Abramovitch, J. Am.
Chem. Soc., 1980, 102, 735-740; (c) P. L. Desbène and N.
Jehanno, J. Heterocycl. Chem., 1984, 21, 1313-1319.
22 (a) E. R. King, E. T. Hennessy and T. A. Betley, J. Am. Chem.
Soc., 2011, 133, 4917-4923; (b) D. A. Iovan and T. A. Betley, J.
Am. Chem. Soc., 2016, 138, 1983-1993; (c) M. J. T. Wilding, D.
A. Iovan and T. A. Betley, J. Am. Chem. Soc., 2017, 139
,
12043-12049; (d) M. J. T. Wilding, D. A. Iovan, A. T. Wrobel, J.
T. Lukens, S. N. MacMillan, K. M. Lancaster and T. A. Betley, J.
Am. Chem. Soc., 2017, 139, 14757-14766.
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