Cobalt-Catalyzed Aerobic Oxidative Dearomatization of 2-Aryl Indoles and in situ [3+2] Annulation with Enamides

doi:10.6023/cjoc202104057

Abstract

An one-pot reaction for the rapid construction of tricyclic fused indoline frameworks from 2-aryl indoles and N-acetyl enamides under oxygen atmosphere has been developed. The notable features of this method involve easy availability of starting materials, simple manipulation, good regio- and diastereo-selectivity, as well as environmentally friendly conditions. Mechanistic studies indicated that this reaction proceeds via oxidative dearomatization and subsequent [3+2] annulation with enamides.

Key words: cobalt-catalysis, oxidative dearomatization, annulation, indoles, enamides

Cite this article

Yinjun Huang, Jinshan Li, Shen Li, Junan Ma. Cobalt-Catalyzed Aerobic Oxidative Dearomatization of 2-Aryl Indoles and in situ [3+2] Annulation with Enamides[J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 4028-4038.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 7

References 18

[1]	(a) Fattorusso, E.; Taglialatela-Scafati, O. Modern Alkaloids: Structure, Isolation, Synthesis and Biology, Wiley-VCH, Weinheim, 2008. pmid: 25255204
	(b) Crich, D.; Banerjee, A. Acc. Chem. Res. 2007, 40, 151. doi: 10.1021/ar050175j pmid: 25255204
	(c) Ruiz-Sanchis, P.; Savina, S. A.; Albericio, F.; Álvarez, M. Chem.-Eur. J. 2011, 17, 1388. doi: 10.1002/chem.201001451 pmid: 25255204
	(d) Vitaku, E.; Smith, D. T.; Njardarson, J. T. J. Med. Chem. 2014, 57, 10257. doi: 10.1021/jm501100b pmid: 25255204
[2]	For reviews, see: (a) Roche, S. P.; Porco Jr., J. A. Angew. Chem. Int. Ed. 2011, 50, 4068. doi: 10.1002/anie.v50.18 pmid: 30839047
	(b) Zhuo, C.-X.; Zhang, W.; You, S.-L. Angew. Chem. Int. Ed. 2012, 51, 12662. doi: 10.1002/anie.201204822 pmid: 30839047
	(c) Repka, L. M.; Reisman, S. E. J. Org. Chem. 2013, 78, 12314. doi: 10.1021/jo4017953 pmid: 30839047
	(d) Ding, Q.; Zhou, X.; Fan, R. Org. Biomol. Chem. 2014, 12, 4807. doi: 10.1039/C4OB00371C pmid: 30839047
	(e) Roche, S. P.; Youte Tendoung, J.-J.; Tréguier, B. Tetrahedron 2015, 71, 3549. doi: 10.1016/j.tet.2014.06.054 pmid: 30839047
	(f) Zheng, C.; You, S.-L. Chem 2016, 1, 830. doi: 10.1016/j.chempr.2016.11.005 pmid: 30839047
	(g) Bariwal, J.; Voskressensky, L. G.; Van der Eycken, E. V. Chem. Soc. Rev. 2018, 47, 3831. doi: 10.1039/C7CS00508C pmid: 30839047
	(h) Wang, Y.; Xie, F.; Lin, B.; Cheng, M.; Liu, Y. Chem.-Eur. J. 2018, 24, 14302. doi: 10.1002/chem.201800775 pmid: 30839047
	(i) Norwood IV, V. M.; Huigens III, R. W. ChemBioChem 2019, 20, 2273. doi: 10.1002/cbic.v20.18 pmid: 30839047
	(j) Zeidan, N.; Lautens, M. Synthesis 2019, 51, 4137. doi: 10.1055/s-0037-1611918 pmid: 30839047
	(k) Zheng, C.; You, S.-L. Nat. Prod. Rep. 2019, 36, 1589. doi: 10.1039/c8np00098k pmid: 30839047
	(l) Zhu, M.; Zhang, X.; You, S. Chem. J. Chin. Univ. 2020, 41, 1407. (in Chinese) pmid: 30839047
	朱敏, 张霄, 游书力, 高等学校化学学报, 2020, 41, 1407.) pmid: 30839047
	For selected recent examples, see: (m) Huang, L.; Cai, Y.; Zhang, H.-J.; Zheng, C.; Dai, L.-X.; You, S.-L. CCS Chem. 2019, 1, 106. pmid: 30839047
	(n) Yang, P.; Xu, R.-Q.; Zheng, C.; You, S.-L. Chin. J. Chem. 2020, 38, 235. doi: 10.1002/cjoc.v38.3 pmid: 30839047
	(o) Yuan, W.-C.; Zhou, X.-J.; Zhao, J.-Q.; Chen, Y.-Z.; You, Y.; Wang, Z.-H. Org. Lett. 2020, 22, 7088. doi: 10.1021/acs.orglett.0c02350 pmid: 30839047
	(p) Gao, X.; Yuan, Y.; Xie, X.; Zhang, Z. Chem. Commun. 2020, 56, 14047. doi: 10.1039/D0CC05672C pmid: 30839047
	(q) Zhu, M.; Huang, X.-L.; Xu, H.; Zhang, X.; Zheng, C.; You, S.-L. CCS Chem. 2021, 3, 652. doi: 10.31635/ccschem.020.202000254 pmid: 30839047
	(r) Wang, R.; Xu, L.; Lu, Y.; Jiang, B.; Hao, W. Chin. J. Org. Chem. 2021, 41, 1582. doi: 10.6023/cjoc202101003 pmid: 30839047
[3]	For review, see: Zhuo, C.-X.; Zheng, C.; You, S.-L. Acc. Chem. Res. 2014, 47, 2558. doi: 10.1021/ar500167f
[4]	For review, see: Denizot, N.; Tomakinian, T.; Beaud, R.; Kouklovsky, C.; Vincent, G. Tetrahedron Lett. 2015, 56, 4413. doi: 10.1016/j.tetlet.2015.05.078
[5]	For review, see: Liang, X.-W.; Zheng, C.; You, S.-L. Chem.-Eur. J. 2016, 22, 11918. doi: 10.1002/chem.201600885
[6]	For review, see: Huang, G.; Yin, B. Adv. Synth. Catal. 2019, 361, 405. doi: 10.1002/adsc.v361.3
[7]	For selected examples, see: (a) Schkeryantz, J. M.; Woo, J. C. G.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 7025. doi: 10.1021/ja00131a035 pmid: 12733890
	(b) Sunazuka, T.; Hirose, T.; Shirahata, T.; Harigaya, Y.; Hayashi, M.; Komiyama, K.; Ōmura, S.; Smith, A. B. J. Am. Chem. Soc. 2000, 122, 2122. doi: 10.1021/ja9938074 pmid: 12733890
	(c) Baran, P. S.; Guerrero, C. A.; Corey, E. J. J. Am. Chem. Soc. 2003, 125, 5628. pmid: 12733890
	(d) May, J. P.; Fournier, P.; Pellicelli, J.; Patrick, B. O.; Perrin, D. M. J. Org. Chem. 2005, 70, 8424. doi: 10.1021/jo051105t pmid: 12733890
	(e) May, J. P.; Patrick, B. O.; Perrin, D. M. Synlett 2006, 3403. pmid: 12733890
	(f) González-Vera, J. A.; Teresa García-López, M.; Herranz, R. Tetrahedron 2007, 63, 9229. doi: 10.1016/j.tet.2007.06.053 pmid: 12733890
	(g) Tu, D.; Ma, L.; Tong, X.; Deng, X.; Xia, C. Org. Lett. 2012, 14, 4830. doi: 10.1021/ol302158h pmid: 12733890
	(h) Zhao, L.; May, J. P.; Huang, J.; Perrin, D. M. Org. Lett. 2012, 14, 90. doi: 10.1021/ol202880y pmid: 12733890
	(i) Han, L.; Liu, C.; Zhang, W.; Shi, X.-X.; You, S.-L. Chem. Commun. 2014, 50, 1231. doi: 10.1039/C3CC47921H pmid: 12733890
	(j) Peng, Q.-L.; Luo, S.-P.; Xia, X.-E.; Liu, L.-X.; Huang, P.-Q. Chem. Commun. 2014, 50, 1986. doi: 10.1039/c3cc48833k pmid: 12733890
	(k) Xu, C.-P.; Luo, S.-P.; Wang, A.-E.; Huang, P.-Q. Org. Biomol. Chem. 2014, 12, 2859. doi: 10.1039/c4ob00314d pmid: 12733890
	(l) Han, L.; Zhang, W.; Shi, X.-X.; You, S.-L. Adv. Synth. Catal. 2015, 357, 3064. doi: 10.1002/adsc.201500557 pmid: 12733890
	(m) Liu, Z.-J.; Huang, P.-Q. J. Org. Chem. 2019, 84, 5627. doi: 10.1021/acs.joc.9b00573 pmid: 12733890
	(n) Sawano, T.; Yamamoto, H. ACS Catal. 2019, 9, 3384. doi: 10.1021/acscatal.9b00840 pmid: 12733890
[8]	(a) Sang, P.; Xie, Y.; Zou, J.; Zhang, Y. Adv. Synth. Catal. 2012, 354, 1873. doi: 10.1002/adsc.v354.10
	(b) Huang, H.; Cai, J.; Ji, X.; Xiao, F.; Chen, Y.; Deng, G.-J. Angew. Chem. Int. Ed. 2016, 55, 307. doi: 10.1002/anie.201508076
	(c) Yamashita, M.; Nishizono, Y.; Himekawa, S.; Iida, A. Tetrahedron 2016, 72, 4123. doi: 10.1016/j.tet.2016.05.054
[9]	For selected examples, see: (a) Capdevielle, P.; Maumy, M. Tetrahedron Lett. 1993, 34, 2953. pmid: 31157355
	(b) Yamashita, M.; Iida, A. Tetrahedron Lett. 2014, 55, 2991. doi: 10.1016/j.tetlet.2014.03.128 pmid: 31157355
	(c) Lin, F.; Chen, Y.; Wang, B.; Qin, W.; Liu, L. RSC Adv. 2015, 5, 37018. doi: 10.1039/C5RA04106F pmid: 31157355
	(d) Guchhait, S. K.; Chaudhary, V.; Rana, V. A.; Priyadarshani, G.; Kandekar, S.; Kashyap, M. Org. Lett. 2016, 18, 1534. doi: 10.1021/acs.orglett.6b00244 pmid: 31157355
	(e) Zhang, C.; Li, S.; Bureš, F.; Lee, R.; Ye, X.; Jiang, Z. ACS Catal. 2016, 6, 6853. doi: 10.1021/acscatal.6b01969 pmid: 31157355
	(f) Cao, W.-B.; Chu, X.-Q.; Zhou, Y.; Yin, L.; Xu, X.-P.; Ji, S.-J. Chem. Commun. 2017, 53, 6601. doi: 10.1039/C7CC02815F pmid: 31157355
	(g) Deng, Z.; Peng, X.; Huang, P.; Jiang, L.; Ye, D.; Liu, L. Org. Biomol. Chem. 2017, 15, 442. doi: 10.1039/C6OB02285E pmid: 31157355
	(h) Liu, X.-X.; Luo, X.-L.; Wu, Z.-Y.; Cui, X.-F.; Zhou, X.-Q.; He, Y.-Q.; Huang, G.-S. J. Org. Chem. 2017, 82, 2107. doi: 10.1021/acs.joc.6b02893 pmid: 31157355
	(i) Cao, W.-B.; Liu, B.-B.; Xu, X.-P.; Ji, S.-J. Org. Chem. Front. 2018, 5, 1194. doi: 10.1039/C7QO01154G pmid: 31157355
	(j) Guo, S.; Wang, F.; Tao, L.; Zhang, X.; Fan, X. J. Org. Chem. 2018, 83, 3889. doi: 10.1021/acs.joc.8b00231 pmid: 31157355
	(k) Zhou, X.-Y.; Chen, X.; Wang, L.-G.; Yang, D.; Li, J.-H. Synlett 2018, 29, 835. doi: 10.1055/s-0036-1591876 pmid: 31157355
	(l) Ding, X.; Dong, C.-L.; Guan, Z.; He, Y.-H. Angew. Chem. Int. Ed. 2019, 58, 118. doi: 10.1002/anie.201811085 pmid: 31157355
	(m) Jiang, X.; Zhu, B.; Lin, K.; Wang, G.; Su, W.-K.; Yu, C. Org. Biomol. Chem. 2019, 17, 2199. doi: 10.1039/C8OB03057J pmid: 31157355
	(n) Liu, X.; Yan, X.; Tang, Y.; Jiang, C.-S.; Yu, J.-H.; Wang, K.; Zhang, H. Chem. Commun. 2019, 55, 6535. doi: 10.1039/C9CC02956G pmid: 31157355
	(o) Liu, X.; Yan, X.; Yu, J.-H.; Tang, Y.-D.; Wang, K.; Zhang, H. Org. Lett. 2019, 21, 5626. doi: 10.1021/acs.orglett.9b01965 pmid: 31157355
	(p) Patel, O. P. S.; Dhiman, S.; Khan, S.; Shinde, V. N.; Jaspal, S.; Srivathsa, M. R.; Jha, P. N.; Kumar, A. Org. Biomol. Chem. 2019, 17, 5962. doi: 10.1039/c9ob00797k pmid: 31157355
	(q) Shukla, G.; Dahiya, A.; Alam, T.; Patel, B. K. Asian J. Org. Chem. 2019, 8, 2243. doi: 10.1002/ajoc.v8.12 pmid: 31157355
	(r) Zhang, L.-L.; Cao, W.-B.; Xu, X.-P.; Ji, S.-J. Org. Chem. Front. 2019, 6, 1787. doi: 10.1039/C9QO00379G pmid: 31157355
	(s) Lu, F.-Y.; Chen, Y.-J.; Chen, Y.; Ding, X.; Guan, Z.; He, Y.-H. Chem. Commun. 2020, 56, 623. doi: 10.1039/C9CC09178E pmid: 31157355
[10]	For reviews, see: (a) Carbery, D. R. Org. Biomol. Chem. 2008, 6, 3455. doi: 10.1039/b809319a pmid: 19082143
	(b) Matsubara, R.; Kobayashi, S. Acc. Chem. Res. 2008, 41, 292. doi: 10.1021/ar700098d pmid: 19082143
[11]	For selected examples, see: (a) Hayashi, Y.; Gotoh, H.; Masui, R.; Ishikawa, H. Angew. Chem. Int. Ed. 2008, 47, 4012. doi: 10.1002/anie.v47:21
	(b) Zu, L.; Xie, H.; Li, H.; Wang, J.; Yu, X.; Wang, W. Chem.-Eur. J. 2008, 14, 6333. doi: 10.1002/chem.200800829
	(c) Noole, A.; Borissova, M.; Lopp, M.; Kanger, T. J. Org. Chem. 2011, 76, 1538. doi: 10.1021/jo200095e
	(d) Wan, J.-P.; Loh, C. C. J.; Pan, F.; Enders, D. Chem. Commun. 2012, 48, 10049. doi: 10.1039/c2cc35644a
	(e) Ding, X.-F.; Su, R.-H.; Yang, W.-L.; Deng, W.-P. Adv. Synth. Catal. 2018, 360, 4168. doi: 10.1002/adsc.v360.21
[12]	(a) Qiao, B.; Cao, H.-Q.; Huang, Y.-J.; Zhang, Y.; Nie, J.; Zhang, F.-G.; Ma, J.-A. Chin. J. Chem. 2018, 36, 809. doi: 10.1002/cjoc.v36.9 pmid: 32223256
	(b) Feng, F.-F.; Li, J.-S.; Li, S.; Ma, J.-A. Adv. Synth. Catal. 2019, 361, 4222. doi: 10.1002/adsc.v361.18 pmid: 32223256
	(c) Feng, F.-F.; Li, S.; Cheung, C. W.; Ma, J.-A. Org. Lett. 2019, 21, 8419. doi: 10.1021/acs.orglett.9b03181 pmid: 32223256
	(d) Cao, H.-Q.; Liu, H.-N.; Liu, Z.-Y.; Qiao, B.-K.; Zhang, F.-G.; Ma, J.-A. Chem.-Eur. J. 2020, 26, 5515. doi: 10.1002/chem.v26.24 pmid: 32223256
	(e) Zhang, Y.; Li, J.-K.; Zhang, F.-G.; Ma, J.-A. J. Org. Chem. 2020, 85, 5580. doi: 10.1021/acs.joc.0c00436 pmid: 32223256
	(f) Cao, H.-Q.; Liu, H.-N.; Liu, Z.-Y.; Qiao, B.-K.; Zhang, F.-G.; Ma, J.-A. Org. Lett. 2020, 22, 6414. doi: 10.1021/acs.orglett.0c02229 pmid: 32223256
[13]	For reviews, see: Shi, Z.; Zhang, C.; Tang, C.; Jiao, N. Chem. Soc. Rev. 2012, 41, 3381. doi: 10.1039/c2cs15224j
[14]	(a) Dufour-Ricroch, M. N.; Gaudemer, A. Tetrahedron Lett. 1976, 17, 4079. doi: 10.1016/S0040-4039(00)92580-2
	(b) Nishinaga, A.; Tomita, H. J. Mol. Catal. 1980, 7, 179. doi: 10.1016/0304-5102(80)85017-6
	(c) Niederhoffer, E. C.; Timmons, J. H.; Martell, A. E. Chem. Rev. 1984, 84, 137. doi: 10.1021/cr00060a003
	(d) Bailey, C. L.; Drago, R. S. Coord. Chem. Rev. 1987, 79, 321. doi: 10.1016/0010-8545(87)80009-7
[15]	For preparation of 6, see: Li, J.-S.; Liu, Y.-J.; Zhang, G.-W.; Ma, J.-A. Org. Lett. 2017, 19, 6364. doi: 10.1021/acs.orglett.7b03213
[16]	(a) Li, P.; Yong, W.; Sheng, R.; Rao, W.; Zhu, X.; Zhang, X. Adv. Synth. Catal. 2019, 361, 201. doi: 10.1002/adsc.v361.1
	(b) Reiss, H.; Shalit, H.; Vershinin, V.; More, N. Y.; Forckosh, H.; Pappo, D. J. Org. Chem. 2019, 84, 7950. doi: 10.1021/acs.joc.9b00822
[17]	Lian, X.-L.; Lei, H.; Quan, X.-J.; Ren, Z.-H.; Wang, Y.-Y.; Guan, Z.-H. Chem. Commun. 2013, 49, 8196. doi: 10.1039/c3cc44215b
[18]	Reeves, J. T.; Tan, Z.; Han, Z. S.; Li, G.; Zhang, Y.; Xu, Y.; Reeves, D. C.; Gonnella, N. C.; Ma, S.; Lee, H.; Lu, B. Z.; Senanayake, C. H. Angew. Chem. Int. Ed. 2012, 51, 1400. doi: 10.1002/anie.201107601

Entry	Catalyst	Solvent	Time/h	Yield^b/%	dr^c
1	Co(salophen)	CH₂Cl₂	48	72	4∶1
2	Co(TPP)	CH₂Cl₂	24^d	72	4∶1
3	Co(TPP)	CHCl₃	6^e	82	4∶1
4	Co(TPP)	CCl₄	12^f	64	4∶1
5	Co(TPP)	DCE	48	28	4∶1
6	Co(TPP)	Et₂O	48	10	2∶1
7	Co(TPP)	THF	48	34	5∶1
8	Co(TPP)	Toluene	48	25	4∶1

Entry	Catalyst	Solvent	Time/h	Yield^b/%	dr^c
1	Co(salophen)	CH₂Cl₂	48	72	4∶1
2	Co(TPP)	CH₂Cl₂	24^d	72	4∶1
3	Co(TPP)	CHCl₃	6^e	82	4∶1
4	Co(TPP)	CCl₄	12^f	64	4∶1
5	Co(TPP)	DCE	48	28	4∶1
6	Co(TPP)	Et₂O	48	10	2∶1
7	Co(TPP)	THF	48	34	5∶1
8	Co(TPP)	Toluene	48	25	4∶1

钴催化2-芳基吲哚氧化去芳构化及与烯酰胺[3+2]环化反应