3
62
63
64
358, 774. c) K. Parthasarathy, C.-H. Cheng, J. Org. Chem. 2009,
74, 9359. d) J. Li, M. Tang, L. Zang, X. Zhang, Z. Zhang, L.
Ackermann, Org. Lett. 2016, 18, 2742.
1
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3
4
5
6
7
8
9
In summary, we have developed a Rh(III)-catalyzed
direct coupling reaction of 3-aryl-1,2,4-oxadiazoles and
alkynes. The oxadiazole ring works as directing group as
well as formal oxidizing reagent to ensure the catalytic
turnover. This protocol appears to be an effective method
for the synthesis of 1-aminoisoquinoline derivatives of
interest in pharmaceutical chemistry.
65 11 L. L. Whitfield, E. P. Papadopoulos, J. Heterocycl. Chem. 1981,
66
18, 1197.
67 12 Z. Wan, A. Hall, Y. Sang, J.-N. Xiang, E. Yang, B. Smith, D. C.
68
69
70
71
Harrison, G. Yang, H. Yu, H. S. Price, J. Wang, J. Hawkins, L.-F.
Lau, M. R. Johnson, T. Li, W. Zhao, W. L. Mitchell, X. Su, X.
Zhang, Y. Zhou, Y. Jin, Z. Tong, Z. Cheng, I. Hussain, J. D.
Elliott, Y. Matsuoka, Bioorg. Med. Chem. Lett. 2011, 21, 4832.
This work was supported by JSPS KAKENHI (Grant Nos.
72 13 During the preparation of this manuscript, a similar reaction
10 JP 24225002 and JP 17H06092) and the Deutsche
11 Forschungsgemeinschaft through the International Research
12 Training Group Seleca (IGRK 1628).
13
73
74
using a Co(III) catalyst was reported: F. Yang, J. Yu, Y. Liu, J.
Zhu, Org. Lett. 2017, 19, 2885.
75 14 For details, see the Supporting Information.
76 15 D. R. Stuart, M. Bertrand-Laperle, K. M. N. Burgess and K.
77
Fagnou, J. Am. Chem. Soc. 2008, 130, 16474.
14 Supporting
Information
is
available
on
15 http://dx.doi.org/10.1246/cl.******.
16 References and Notes
1
a) J. D. Scott, R. M. Williams, Chem. Rev. 2002, 102, 1669. b) V.
G. Kartsev, Med. Chem. Res. 2004, 13, 325. c) K. W. Bentley,
Nat. Prod. Req. 2004, 21, 395. d) Bentley, K. W. Nat. Prod. Req.
2006, 23, 444. e) K. Bhadra, G. S. Kumar, Med. Res. Rev. 2011,
31, 821.
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
2
a) C. W. Lim, O. Tissot, A. Mattison, M. W. Hooper, J. M.
Brown, A. R. Cowley, D. I. Hulmes, A. Blacker, J. Org. Process
Res. Dev. 2003, 7, 379. b) B. A. Sweetman, H. MüllerBunz, P. J.
Guiry, Tetrahedron Lett. 2005, 46, 4643. c) F. Durola, J.-P.
Sauvage, O. S. Wenger, Chem. Commun. 2006, 171.
a) N. Guimond, K. Fagnou, J. Am. Chem. Soc. 2009, 131, 12050.
b) T. Fukutani, N. Umeda, K. Hirano, T. Satoh, M. Miura, Chem.
Commun. 2009, 5141. c) K. Morimoto, K. Hirano, T. Satoh, M.
Miura, Chem. Lett. 2011, 40, 600.
3
4
a) P. C. Too, Y.-F. Wang, S. Chiba, Org. Lett. 2010, 12, 5688. b)
P. C. Too, S. H. Chua, S. H. Wong, S. Chiba, J. Org. Chem.
2011, 76, 6159. c) J. Jayakumar, K. Parthasarathy, Y.-H. Chen,
T.-H. Lee, S.-C. Chuang, C.-H. Cheng, Angew. Chem. Int. Ed.
2014, 53, 9889. d) T. K. Hyster, T. Rovis, Chem. Commun. 2011,
47, 11846. e) N. Guimond, S. I. Gorelsky, K. Fagnou, J. Am.
Chem. Soc. 2011, 133, 6449. f) X. Zhang, D. Chen, M. Zhao, J.
Zhao, A. Jia, X. Li, Adv. Synth. Catal. 2011, 353, 719. g) D.
Zhao, F. Lied, F. Glorius, Chem. Sci. 2014, 5, 2869. h) L. Zheng,
J. Ju, Y. Bin, R. Hua, J. Org. Chem. 2012, 77, 5794.
a) R. K. Chinnagolla, S. Pimparkar, M. Jeganmohan, Chem.
Commun. 2013, 49, 3703. b) C. Kornhaaß, J. Li, L. Ackermann,
J. Org. Chem. 2012, 77, 9190. c) R. K. Chinnagolla, S.
Pimparkar, M. Jeganmohan, Org. Lett. 2012, 14, 3032.
Selected recent examples for C-H activation using internal
oxidant to construct N-containing heterocyclic compounds, see;
a) Y. Tan, J. F. Hartwig, J. Am. Chem. Soc. 2010, 132, 3676. b)
N. Guimond, C. Gouliaras, K. Fagnou, J. Am. Chem. Soc. 2010,
132, 6908. c) H. Wang, F. Glorius, Angew. Chem. Int. Ed. 2012,
51, 7318. e) J. M. Neely, T. Robis, J. Am. Chem. Soc. 2013, 135,
66. f) R. B. Dateer, S. Chang, J. Am. Chem. Soc. 2015, 137, 4908.
g) X. Yu, K. Chen, Q. Wang, S. Guo, S. Zha, J. Zhu, Angew.
Chem. Int. Ed. 2017, 56, 5222.
5
6
7
a) S.-C. Chuang, P. Gandeepan, C.-H. Cheng, Org. Lett. 2013, 15,
5750. b) Y.-F. Wang, K. K. Toh, J.-Y. Lee, S. Chiba, Angew.
Chem. Int. Ed. 2011, 50, 5927.
D. Takeda, K. Hirano, T. Satoh, M. Miura Heterocycles 2012, 86,
487.
Transition metal-catalyzed 1-aminoisoquinoline synthesis using
amidines, see; a) J. Li, M. John, L. Ackermann, Chem. Eur. J.
2014, 20, 5403. b) X. Wei, M. Zhao, Z. Du, X. Li, Org. Lett.
2011, 13, 4636.
8
9
58 10 Transition metal-catalyzed 1-aminoisoquinoline synthesis using
59
60
61
amidoxime derivatives, see; a) X. Yu, K. Chen, F. Yang, S. Zha,
J. Zhu, Org. Lett. 2016, 18, 5412. b) K. Muralirajan, R.
Kuppusamy, S. Prakash, C.-H. Cheng, Adv. Synth. Catal. 2016,