ChemComm
DOI: 10.1039/C5CC00P78a0gAe 4 of 4
(g) A. W. Schammel, G. Chiou and N. K. Garg, J. Org. Chem. 2012,
12 For details, see the Supporting Information.
77, 725; (h) T. Araki, T. Ozawa, H. Yokoe, M. Kanematsu, M.
Yoshida and K. Shishido, Org. Lett. 2013, 15, 200.
5
6
For recent reviews on dearomatization reaction of indoles, see: (a) S.
P. Roche and J. A. Porco Jr, Angew. Chem., Int. Ed. 2011, 50, 4068;
(b) C.-X. Zhuo, W. Zhang and S.-L. You, Angew. Chem., Int. Ed.
2012, 51, 12662; (c) L. M. Repka and S. E. Reisman, J. Org. Chem.
2013, 78, 12314.
5
10
15
20
25
30
35
40
45
50
55
60
For selected organocatalyzed dearomatization of indoles, see: (a) J. F.
Austin, S.-G. Kim, C. J. Sinz, W.-J. Xiao and D. W. C. MacMillan,
Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5482; (b) C. Gioia, A.
Hauville, L. Bernardi, F. Fini and A. Ricci, Angew. Chem., Int. Ed.
2008, 47, 9236; (c) S. B. Jones, B. Simmons, A. Mastracchio and
D. W. C. MacMillan, Nature. 2011, 475, 183; (d) O. Lozano, G.
Blessley, T. M. del Campo, A. L. Thompson, G. T. Giuffredi, M.
Bettati, M. Walker, R. Borman and V. Gouverneur, Angew. Chem.,
Int. Ed. 2011, 50, 8105; (e) F. Kolundzic, M. N. Noshi, M. Tjandra,
M. Movassaghi and S. J. Miller, J. Am. Chem. Soc. 2011, 133, 9104;
(f) B. Tan, G. Hernández-Torres and C. F. Barbas, III. J. Am. Chem.
Soc. 2011, 133, 12354; (g) Z. Zhang and J. C. Antilla, Angew.
Chem., Int. Ed. 2012, 51, 11778; (h) W. Xie, G. Jiang, H. Liu, J. Hu,
X. Pan, H. Zhang, X. Wan, Y. Lai and D. Ma, Angew. Chem., Int.
Ed. 2013, 52, 12924; (i) T. M. Kaiser and J. Yang, Eur. J. Org.
Chem. 2013, 3983. (j) H. M. Nelson, S. H. Reisberg, H. P.
Shunatona, J. S. Patel and F. D. Toste, Angew. Chem., Int. Ed. 2014,
53, 5600; (k) L. Liao, C. Shu, M. Zhang, Y. Liao, X. Hu, Y. Zhang,
Z. Wu, W. Yuan and X. Zhang, Angew. Chem., Int. Ed. 2014, 53,
10471; (l) C. S. Yeung, R. E. Ziegler, J. A. Porco Jr and E. N.
Jacobsen, J. Am. Chem. Soc. 2014, 136, 13614. (m) Y.-C. Zhang, J.-
J. Zhao, F. Jiang, S.-B. Sun and F. Shi, Angew. Chem., Int. Ed.
2014, 53, 13912.
For selected metal-catalyzed dearomatization of indoles, see: (a) M.
Kimura, M. Futamata, R. Mukai and Y. Tamaru, J. Am. Chem. Soc.
2005, 127, 4592; (b) B. M. Trost and J. Quancard, J. Am. Chem.
Soc. 2006, 128, 6314; (c) Y. Lian and H. M. L. Davies, J. Am.
Chem. Soc. 2010, 132, 440; (d) L. M. Repka, J. Ni and S. E.
Reisman, J. Am. Chem. Soc. 2010, 132, 14418; (e) N. Shimada, T.
Oohara, J. Krishnamurthi, H. Nambu and S. Hashimoto, Org. Lett.
2011, 13, 6284; (f) S. Zhu and D. W. C. MacMillan, J. Am. Chem.
Soc. 2012, 134, 10815; (g) G. Cera, M. Chiarucci, A. Mazzanti, M.
Mancinelli and M. Bandini, Org. Lett. 2012, 14, 1350; (h) M. E.
Kieffer, K. V. Chuang and S. E. Reisman, Chem. Sci. 2012, 3, 3170;
(i) Y. Liu and H. Du, Org. Lett. 2013, 15, 740; (j) J. Chen and M. J.
Cook, Org. Lett. 2013, 15, 1088; (k) T. D. Montgomery, Y. Zhu, N.
Kagawa and V. H. Rawal, Org. Lett. 2013, 15, 1140; (l) Y.-Q.
Zhang, Y.-A. Yuan, G.-S. Liu and H. Xu, Org. Lett. 2013, 15, 3910;
(m) M. E. Kieffer, K. V. Chuang and S. E. Reisman, J. Am. Chem.
Soc. 2013, 135, 5557; (n) J. E. Spangler and H. M. L. Davies, J. Am.
Chem. Soc. 2013, 135, 6802; (o) H. Xiong, H. Xu, S. Liao, Z. Xie
and Y. Tang, J. Am. Chem. Soc. 2013, 135, 7851; (p) M.-C. Tong,
X. Chen, J. Li, R. Huang, H. Tao and C.-J. Wang, Angew. Chem.,
Int. Ed. 2014, 53, 4680.
7
8
For selected examples, see: (a) C. Liu, W. Zhang, L.-X. Dai and S.-L.
You, Org. Lett. 2012, 14, 4525; [Corrections: Org. Lett. 2012, 14,
5168]; (b) Q. Cai, C. Liu, X.-W. Liang and S.-L. You, Org. Lett.
2012, 14, 4588; (c) X. Zhang, Z.-P. Yang, C. Liu and S.-L. You,
Chem. Sci. 2013, 4, 3239; (d) Q. Cai, Q. Yin and S.-L. You, Asian J.
Org. Chem. 2014, 3, 408; (e) X. Zhang, L. Han and S.-L. You,
Chem. Sci. 2014, 5, 1059; (f) L. Han, C. Liu, W. Zhang, X.-X. Shi
and S.-L. You, Chem. Commun. 2014, 50, 1231; (g) D.-H. Duan, Q.
Yin, S.-G. Wang and S.-L. You, Acta Chim. Sinica 2014, 72, 1001.
(h) Q. Yin and S.-L. You, Org. Lett. 2014, 16, 2426.
9
(a) A. Gualandi, E. Emer, M. G. Capdevila and P. G. Cozzi, Angew.
Chem., Int. Ed. 2011, 50, 7842; (b) A. Gualandi, D. Petruzziello, E.
Emer and P. G. Cozzi, Chem. Commun. 2012, 48, 3614.
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70
10 For an early preparation of C3-methyl substituted pyrrolodindolines
from tryptamines, see: M. Kawahra, A. Nishida and M. B.
Nakagawa, Org. Lett. 2000, 2, 675.
11 When methyl (2-(1H-indol-3-yl)ethyl)carbamate was employed as a
substrate, a dearomatized product with an indole-N substitued by
dithiane was isolated (60% yield).
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