Paper
Organic & Biomolecular Chemistry
S. Balasubramanian, Chem. Commun., 2008, 44, 3055;
(g) H. Zhang, J. Drewe, B. Tseng, S. Kashibhatla and X. Cai,
Bioorg. Med. Chem. Lett., 2004, 12, 3649; (h) H. Zhang,
J. Drewe, B. Tseng, S. Kasibhatla and S. X. Cai, Bioorg. Med.
Chem., 2014, 12, 3649; (i) W. Hu, Z. Guo, F. Chu, A. Bai,
X. Yi, G. Cheng and J. Li, Bioorg. Med. Chem. Lett., 2003, 11,
1153.
2 C. B. Bheeter, L. Chen, J. Soule and H. Doucet, Catal. Sci.
Technol., 2016, 6, 2005–2049 (Review).
3 (a) G. N. Vaidya, S. Fiske, H. Verma, S. K. Lokhanda and
D. Kumar, Green Chem., 2019, 21, 1448; (b) S. Perato,
B. Large, Q. Lu, A. Gaucher and D. Prim, ChemCatChem,
2017, 9, 389.
Scheme 3 Phenylpyrrole synthesis using pyrroles and cyclohexanone.
4 B. Jamwal, M. Kaur, H. Sharma, C. Khajuria, S. Paul and
J. H. Clark, New J. Chem., 2019, 43, 4919.
Conclusions
We have accomplished the Nb2O5/C and Pd/C-catalyzed 3-ary-
lindole synthesis using indoles and cyclohexanone derivatives
as aryl sources. The catalysts can be directly used without pre-
activation and any additional oxidants, and the reaction only
produces water and hydrogen as by-products. Since hetero-
geneous catalysts are easily removable from the reaction
mixture, it is valuable from the viewpoint of green sustainable
chemistry. 3-Cyclohexylindoles (5) as by-products also possess
useful backbones for anti-HCV drugs.25 Therefore, the pre-
sented environmentally-friendly method to construct 3-arylin-
doles as well as 3-cyclohexylindoles can be effectively utilized
in various chemical fields.
5 (a) J. Zhou, P. Hu, M. Zhang, S. J. Huang, M. Wang and
W. P. Su, Chem. – Eur. J., 2010, 16, 5876; (b) J. Cornella,
P. F. Lu and I. Larrosa, Org. Lett., 2009, 11, 5506.
6 N. A. Bumagin, E. V. Luzikova, L. I. Sukhomlinova,
T. P. Tolstaya and I. P. Beletskaya, Russ. Chem. Bull., 1995,
44, 385.
7 M. Yamaguchi, K. Suzuki, Y. Sato and K. Manabe, Org.
Lett., 2017, 19, 5388.
8 Y. Chen, S. Guo, K. Li, J. Qu, H. Yuan, Q. Hua and B. Chen,
Adv. Synth. Catal., 2013, 355, 711.
9 (a) C. He, S. Fan and X. Zhang, J. Am. Chem. Soc., 2010, 132,
12850; (b) D. R. Stuart and K. Fagnou, Science, 2007, 316,
1172.
10 (a) S. Vásquez-Céspedes, K. M. Chepiga, N. Möller,
A. H. Schäfer and F. Glorius, ACS Catal., 2016, 6, 5954;
(b) S. G. Modha and M. F. Greaney, J. Am. Chem. Soc., 2015,
137, 1416; (c) R. J. Phipps and M. J. Gaunt, Science, 2009,
323, 1593; (d) R. J. Phipps, N. P. Grimster and M. J. Gaunt,
J. Am. Chem. Soc., 2008, 130, 8172.
11 J. Chen and J. Wu, Angew. Chem., Int. Ed., 2017, 56, 3951.
12 Y. Zhang, X. Feng, Y. Yang and B. Cao, Tetrahedron Lett.,
2016, 57, 2298.
13 Review: (a) S. A. Girard, H. Huang, F. Zhou, G. Deng and
C. Li, Org. Chem. Front., 2015, 2, 279; (b) H. Zeng, Z. Qiu,
A. Domínguez-Huerta, Z. Hearne, Z. Chen and C. Li, ACS
Catal., 2017, 7, 510.
14 (a) M. Sutter, R. Lafon, Y. Raoul, E. Métay and M. Lemaire,
Eur. J. Org. Chem., 2013, 5902; (b) M. Sutter, N. Sotto,
Y. Raoul, E. Métay and M. Lemaire, Green Chem., 2013, 15,
347; (c) M. Simon, S. A. Girard and C. Li, Angew, Chem., Int.
Ed., 2012, 51, 7537.
Conflicts of interest
There are no conflicts to declare.
Acknowledgements
We thank the N.E. Chemcat Corporation for the kind gift of
the various metal on carbon catalysts. This study was partially
supported by a Takeda Science Foundation (for Y. S.).
Notes and references
1 (a) C. Li, Y. Xie, F. Xiao, H. Huang and G. Deng, Chem.
Commun., 2019, 55, 4079; (b) N. K. Kaushik, N. Kaushik,
P. Attri, N. Kumar, C. H. Kim, A. K. Verma and E. H. Choi,
Molecules, 2013, 18, 6620; (c) A. P. Kale, G. S. Kumar and
M. Kapur, Org. Biomol. Chem., 2015, 13, 10995; 15 (a) Y. Zeng, B. Wang, Y. Li, X. Yan, L. Chen and Y. Wang,
(d) T. I. Richardson, C. A. Clarke, K. Yu, Y. K. Yee,
T. J. Bleisch, J. E. Lopez, S. A. Jones, A. E. Hughs,
B. S. Muehl, C. W. Lugar, T. L. Moore, P. K. Shetler,
R. W. Zink, J. J. Osborne, C. Montrose-Rafizadeh, N. Patel,
A. G. Geiser, R. J. S. Galvin and J. A. Dodge, ACS Med.
Chem. Lett., 2011, 2, 148; (e) Ö. Gϋzel, A. Maresca,
Ind. Eng. Chem. Res., 2020, 59, 1436; (b) Y. Koizumi, X. Jin,
T. Yatabe, R. Miyazaki, J. Hasegawa, K. Nozaki, N. Mizuno
and K. Yamaguchi, Angew, Chem., Int. Ed., 2019, 58, 10893;
(c) M. Xiong, Z. Gao, X. Liang, P. Cai, H. Zhu and Y. Pan,
Chem. Commun., 2018, 54, 9679; (d) Y. Shimomoto,
R. Matsubara and M. Hayashi, Adv. Synth. Cat., 2018, 360,
3297; (e) Z. Wang, X. Chen, H. Xie, D. Wang, H. Huang and
G. Deng, Org. Lett., 2018, 20, 5470; (f) K. Taniguchi, X. Jin,
K. Yamaguchi, K. Nozaki and N. Mizuno, Chem. Sci., 2017,
R.
A.
Hall,
A.
Scozzafava,
A.
Mastrolorenzo,
F. A. Mϋhlschlegel and C. T. Supuran, Bioorg. Med. Chem.
Lett., 2010, 20, 2508; (f) J. Dash, P. S. Shirude and
Org. Biomol. Chem.
This journal is © The Royal Society of Chemistry 2020