10.1002/chem.202000706
Chemistry - A European Journal
COMMUNICATION
Synth. Catal. 2014, 356, 1521–1526. (f) C.-Y. Tang, Y. Tao, X.-Y. Wu, F.
Sha, Adv. Synth. Catal. 2014, 356, 609–615. (g) H. Baars, Y. Unoh, T.
Okada, K. Hirano, T. Satoh, K. Tanaka, C. Bolm, M. Miura, Chem. Lett.
2014, 43, 1782–1784. (h) S. Peng, S. Liu, S. Zhang, S. Cao, J. Sun, Org.
Lett. 2015, 17, 5032–5035. (i) P. Bai, X.-F. Huang, G.-D. Xu, Z.-Z. Huang,
Org. Lett. 2016, 18, 3058–3061. (j) A. B. Weinstein, J. A. Ellman, Org.
Lett. 2016, 18, 3294–3297. (k) H. Chu, P. Xue, J.-T. Yu, J. Cheng, J. Org.
Chem. 2016, 81, 8009–8013. (l) Q. Wang, X. Li, Org. Chem. Front. 2016,
3, 1159–1162. (m) X. Lin, R. Chauvin, Y. Yu, L. Wang, L. Xu, X. Cui,
ChemistrySelect 2017, 2, 2383–2387.
special thanks for a JSPS Postdoctoral Research Fellowship. We
also wish to thank the Instrumental Analysis Center, Faculty of
Engineering, Osaka University, for assistance with the HRMS.
Keywords: C-H activation • Oxidative coupling • Rh(III) catalyst
• 1-Naphthylamine • Acrylate esters
[1]
Recent reviews on C-H bond activation, see: (a) Z. Chen, B. Wang, J.
Zhang, W. Yu, Z. Liu, Y. Zhang, Org. Chem. Front. 2015, 2, 1107–1295.
(b) Z. Huang, H. N. Lim, F. Mo, M. C. Young, G. Dong, Chem. Soc. Rev.
2015, 44, 7764–7786. (c) T. Gensch, M. N. Hopkinson, F. Glorius, J.
Wencel-Delord, Chem. Soc. Rev. 2016, 45, 2900–2936. (d) J. He, M.
Wasa, K. S. L. Chan, Q. Shao, J.-Q. Yu, Chem. Rev. 2017, 117, 8754–
8786. (e) J. R. Hummel, J. A. Boerth, J. A. Ellman, Chem. Rev. 2017,
117, 9163–9227. (f) Y. Park, Y. Kim, S. Chang, Chem. Rev. 2017, 117,
9247–9301. (g) Y. Yang, J. Lan, J. You, Chem. Rev. 2017, 117, 8787–
8863. (h) C. Sambiagio, D. Schönbauer, R. Blieck, T. Dao-Huy, G.
Pototschnig, P. Schaaf, T. Wiesinger, M. F. Zia, J. Wencel-Delord, T.
Besset, et al., Chem. Soc. Rev. 2018, 47, 6603–6743. (i) A. Dey, S. K.
Sinha, T. K. Achar, D. Maiti, Angew. Chem. Int. Ed. 2019, 58, 10820–
10843. (j) P. Gandeepan, T. Muller, D. Zell, G. Cera, S. Warratz, L.
Ackermann, Chem. Rev. 2019, 119, 2192–2452. (k) S. M. Khake, N.
Chatani, Trends Chem. 2019, 1, 524–539. (l) S. Rej, Y. Ano, N. Chatani,
Chem. Rev. 2020, 120, 1788–1887.
[5]
[6]
For Ru-catalyzed free amine’s C-H functionalization, see: (a) C. Suzuki,
K. Hirano, T. Satoh, M. Miura, Org. Lett. 2013, 15, 3990–3993. (b) P.
Villuendas, E. P. Urriolabeitia, J. Org. Chem. 2013, 78, 5254–5263. (c)
S. Ruiz, P. Villuendas, M. A. Ortuño, A. Lledõs, E. P. Urriolabeitia, Chem.
Eur. J. 2015, 21, 8626–8636. (d) S. Ruiz, F. J. Sayago, C. Cativiela, E.
P. Urriolabeitia, J. Mol. Catal. A Chem. 2017, 426, 407–418.
For the Ir-catalyzed C-H functionalization of free amines, see: (a) H. He,
W.-B. Liu, L.-X. Dai, S.-L. You, J. Am. Chem. Soc. 2009, 131, 8346–8347.
(b) K.-Y. Ye, H. He, W.-B. Liu, L.-X. Dai, G. Helmchen, S.-L. You, J. Am.
Chem. Soc. 2011, 133, 19006–19014. (c) K.-Y. Ye, L.-X. Dai, S.-L. You,
Asian J. Org. Chem. 2013, 2, 244–249. (d) C. Suzuki, K. Hirano, T. Satoh,
M. Miura, Org. Lett. 2015, 17, 1597–1600. (e) H. Chen, M. P. Huestis,
ChemCatChem 2015, 7, 743–746. (f) A. Boelke, L. D. Caspers, B. J.
Nachtsheim, Org. Lett. 2017, 19, 5344–5347. (g) L. D. Caspers, P.
Finkbeiner, B. J. Nachtsheim, Chem. Eur. J. 2017, 23, 2748–2752. (h) K.
Yan, Y. Lin, Y. Kong, B. Li, B. Wang, Adv. Synth. Catal. 2019, 361, 1570–
1575.
[2]
[3]
Reviews on the directing group assisted C-H activation of amine
derivatives, see: (a) S. Agasti, A. Dey, D. Maiti, Chem. Commun. 2017,
53, 6544–6556. (b) J. C. K. Chu, T. Rovis, Angew. Chem. Int. Ed. 2018,
57, 62–101. (c) C. He, W. G. Whitehurst, M. J. Gaunt, Chem 2019, 5,
1031–1058. (d) S. Rej, N. Chatani, Angew. Chem. Int. Ed. 2019, 58,
8304–8329.
[7]
For the Co-catalyzed C-H functionalization of free amines, see: (a) T.-H.
Zhu, S.-Y. Wang, Y.-Q. Tao, T.-Q. Wei, S.-J. Ji, Org. Lett. 2014, 16,
1260–1263. (b) P. Xu, T.-H. Zhu, T.-Q. Wei, S.-Y. Wang, S.-J. Ji, RSC
Adv. 2016, 6, 32467–32470.
[8]
[9]
For a paper on the Cu-mediated C-H functionalization of free amines,
see: R. Morioka, K. Hirano, T. Satoh, M. Miura, Chem. Eur. J. 2014, 20,
12720–12724.
For the Pd-catalyzed C-H functionalization of free amines, see: (a) B.
López, A. Rodriguez, D. Santos, J. Albert, X. Ariza, J. Garcia, J. Granell,
Chem. Commun. 2011, 47, 1054–1056. (b) B. Haffemayer, M. Gulias, M.
J. Gaunt, Chem. Sci. 2011, 2, 312–315. (c) Z. Liang, L. Ju, Y. Xie, L.
Huang, Y. Zhang, Chem. Eur. J. 2012, 18, 15816–15821. (d) Z. Liang, R.
Feng, H. Yin, Y. Zhang, Org. Lett. 2013, 15, 4544–4547. (e) J. Albert, X.
Ariza, T. Calvet, M. Font-Bardia, J. Garcia, J. Granell, A. Lamela, B.
López, M. Martinez, L. Ortega, et al., Organometallics 2013, 32, 649–
659. (f) M. Miura, C.-G. Feng, S. Ma, J.-Q. Yu, Org. Lett. 2013, 15, 5258–
5261. (g) Z. Liang, J. Yao, K. Wang, H. Li, Y. Zhang, Chem. Eur. J. 2013,
19, 16825–16831. (h) A. McNally, B. Haffemayer, B. S. L. Collins, M. J.
Gaunt, Nature 2014, 510, 129–133. (i) A. Rodríguez, J. Albert, X. Ariza,
J. Garcia, J. Granell, J. Farràs, A. La Mela, E. Nicolás, J. Org. Chem.
2014, 79, 9578–9585. (j) C. He, M. J. Gaunt, Angew. Chem. Int. Ed. 2015,
54, 15840–15844. (k) J. Calleja, D. Pla, T. W. Gorman, V. Domingo, B.
Haffemayer, M. J. Gaunt, Nat. Chem. 2015, 7, 1009–1016. (l) Z. Zuo, J.
Liu, J. Nan, L. Fan, W. Sun, Y. Wang, X. Luan, Angew. Chem. Int. Ed.
2015, 54, 15385–15389. (m) H. Taneda, K. Inamoto, Y. Kondo, Org. Lett.
2016, 18, 2712–2715. (n) S. Yugandar, S. Konda, H. Ila, J. Org. Chem.
2016, 81, 2035–2052. (o) K. Chen, D. Wang, Z.-W. Li, Z. Liu, F. Pan, Y.-
F. Zhang, Z.-J. Shi, Org. Chem. Front. 2017, 4, 2097–2101. (p) J. Zhu,
W. Hu, S. Sun, J. T. Yu, J. Cheng, Adv. Synth. Catal. 2017, 359, 3725–
3728. (q) T. U. Thikekar, C.-M. Sun, Adv. Synth. Catal. 2017, 359, 3388–
3396. (r) A. Mancinelli, C. Alamillo, J. Albert, X. Ariza, H. Etxabe, J.
Farràs, J. Garcia, J. Granell, F. J. Quijada, Organometallics 2017, 36,
911–919. (s) D.-Y. Li, S. Liu, S. Chen, A. Wang, X.-P. Zhu, P.-N. Liu,
ACS Catal. 2018, 8, 6407–6412. (t) C. Zhang, Y. Ding, Y. Gao, S. Li, G.
Li, Org. Lett. 2018, 20, 2595–2598. (u) G. Jiang, W. Hu, J. Li, C. Zhu, W.
Wu, H. Jiang, Chem. Commun. 2018, 54, 1746–1749.
For selected papers on the C8-functionalization of 1-naphthylamines,
see: (a) X. Li, X. Gong, M. Zhao, G. Song, J. Deng, X. Li, Org. Lett. 2011,
13, 5808–5811. (b) X. Wang, X. Li, J. Xiao, Y. Jiang, X. Li, Synlett 2012,
23, 1649–1652. (c) E. T. Nadres, G. I. F. Santos, D. Shabashov, O.
Daugulis, J. Org. Chem. 2013, 78, 9689–9714. (d) R. Odani, K. Hirano,
T. Satoh, M. Miura, J. Org. Chem. 2013, 78, 11045–11052. (e) L. Huang,
Q. Li, C. Wang, C. Qi, J. Org. Chem. 2013, 78, 3030–3038. (f) L. Huang,
X. Sun, Q. Li, C. Qi, J. Org. Chem. 2014, 79, 6720–6725. (g) M. Iwasaki,
W. Kaneshika, Y. Tsuchiya, K. Nakajima, Y. Nishihara, J. Org. Chem.
2014, 79, 11330–11338. (h) R. Shang, L. Ilies, E. Nakamura, J. Am.
Chem. Soc. 2015, 137, 7660–7663. (i) Z. Li, S. Sun, H. Qiao, F. Yang, Y.
Zhu, J. Kang, Y. Wu, Y. Wu, Org. Lett. 2016, 18, 4594–4597. (j) J. Lan,
H. Xie, X. Lu, Y. Deng, H. Jiang, W. Zeng, Org. Lett. 2017, 19, 4279–
4282. (k) S. Pradhan, P. B. De, T. Punniyamurthy, J. Org. Chem. 2017,
82, 4883–4890. (l) S. Rej, N. Chatani, ACS Catal. 2018, 8, 6699–6706.
(m) X. Yu, F. Yang, Y. Wu, Y. Wu, Org. Lett. 2019, 21, 1726–1729. (n)
[10] For the importance of alkylidene-1,2-dihydrobenzo[cd]indoles derivatives
as drugs or kinase inhibitors, see: (a) X. Li, Q. Wang, Y. Qing, Y. Lin, Y.
Zhang, X. Qian, J. Cui, Bioorganic Med. Chem. 2010, 18, 3279–3284.
(b) S. H. Sinha, E. A. Owens, Y. Feng, Y. Yang, Y. Xie, Y. Tu, M. Henary,
Y. G. Zheng, Eur. J. Med. Chem. 2012, 54, 647–659. (c) M. Yan, J. Zhao,
D. Sun, W. Sun, B. Zhang, W. Deng, D. Zhang, L. Wang, Tetrahedron
2017, 73, 3355–3362.
[11] For the importance of alkylidene-1,2-dihydrobenzo[cd]indoles as dye,
see: (a) C. Cheng, N. Gao, C. Yu, Z. Wang, J. Wang, E. Hao, Y. Wei, X.
Mu, Y. Tian, C. Ran, et al., Org. Lett. 2015, 17, 278–281. (b) D. Gao, A.
Li, L. Guan, X. Zhang, L. Y. Wang, Dye. Pigment. 2016, 129, 163–173.
[4]
For the Rh-catalyzed C-H functionalization of free amines, see: (a) K.
Morimoto, K. Hirano, T. Satoh, M. Miura, Chem. Lett. 2011, 40, 600–602.
(b) K. Morimoto, M. Itoh, K. Hirano, T. Satoh, Y. Shibata, K. Tanaka, M.
Miura, Angew. Chem. Int. Ed. 2012, 51, 5359–5362. (c) D.-S. Kim, J.-W.
Park, C.-H. Jun, Adv. Synth. Catal. 2013, 355, 2667–2679. (d) Q. Jiang,
D. Duan-Mu, W. Zhong, H. Chen, H. Yan, Chem. Eur. J. 2013, 19, 1903–
1907. (e) C. Suzuki, K. Morimoto, K. Hirano, T. Satoh, M. Miura, Adv.
(c)
M. Matsui, Y. Haishima, Y. Kubota, K. Funabiki, J. Jin, T. H. Kim,
K. Manseki, Dye. Pigment. 2017, 141, 457–462.
[12] For the synthetic procedure of alkylidene-1,2-dihydrobenzo[cd]indoles
see: (a) A. Kamal, G. Ramakrishna, V. Lakshma Nayak, P. Raju, A. V.
Subba Rao, A. Viswanath, M. V. P. S. Vishnuvardhan, S. Ramakrishna,
G. Srinivas, Bioorganic Med. Chem. 2012, 20, 789–800. (b) Q. Wang, L.
For internal use, please do not delete. Submitted_Manuscript
This article is protected by copyright. All rights reserved.