An Oxidant-Free Strategy for Indole Synthesis via Intramolecular C-C Bond Construction under Visible Light Irradiation: Cross-Coupling Hydrogen Evolution Reaction

ACS Catalysis

Volumn 6, Issue 7, 2016, Pages 4635-4639

  Wu, Cheng Juan ^a   Meng, Qing Yuan ^a   Lei, Tao ^a   Zhong, Jian Ji ^a   Liu, Wen Qiang ^a   Zhao, Lei Min ^a   Li, Zhi Jun ^a   Chen, Bin ^a   Tung, Chen Ho ^a   Wu, Li Zhu ^a  

^a TECHNICAL INSTITUTE OF PHYSICS AND CHEMISTRY   (China)

Author keywords

C H functionalization; cross coupling hydrogen evolution; indoles; photochemistry; radical addition

Indexed keywords

AMINES; CHEMICAL REACTIONS; IRRADIATION; OXIDANTS; PHOTOCHEMICAL REACTIONS; PHOTOSENSITIZERS;

C-H FUNCTIONALIZATION; ELECTROCHEMICAL STUDIES; HYDROGEN EVOLUTION; HYDROGEN EVOLUTION REACTIONS; INDOLES; MILD REACTION CONDITIONS; RADICAL ADDITION; VISIBLE-LIGHT IRRADIATION;

LIGHT;

EID: 84977137165     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/acscatal.6b00917     Document Type: Article

References (73)

1. Janicki, S. Z.; Schuster, G. B. J. Am. Chem. Soc. 1995, 117, 8524-8527 10.1021/ja00138a005
2. Somei, M.; Yamada, F. Nat. Prod. Rep. 2004, 21, 278-311 10.1039/b212257j
3. Somei, M.; Yamada, F. Nat. Prod. Rep. 2005, 22, 73-103 10.1039/b316241a
4. Smart, B. P.; Oslund, R. C.; Walsh, L. A.; Gelb, M. H. J. Med. Chem. 2006, 49, 2858-2860 10.1021/jm060136t
5. Ishikura, M.; Yamada, K.; Abe, T. Nat. Prod. Rep. 2010, 27, 1630-1680 10.1039/c005345g
6. Kochanowska-Karamyan, A. J.; Hamann, M. T. Chem. Rev. 2010, 110, 4489-4497 10.1021/cr900211p
7. Robinson, B. Chem. Rev. 1963, 63, 373-401 10.1021/cr60224a003
8. Robinson, B. Chem. Rev. 1969, 69, 227-250 10.1021/cr60258a004
9. Hegedus, L. S. Angew. Chem., Int. Ed. Engl. 1988, 27, 1113-1126 10.1002/anie.198811133
10. Gribble, G. W. Contemp. Org. Synth. 1994, 1, 145-172 10.1039/CO9940100145
11. Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873-2920 10.1021/cr040639b
12. Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875-2911 10.1021/cr0505270
13. Krüger, K.; Tillack, A.; Beller, M. Adv. Synth. Catal. 2008, 350, 2153-2167 10.1002/adsc.200800409
14. Cacchi, S.; Fabrizi, G. Chem. Rev. 2011, 111, PR215-PR283 10.1021/cr100403z
15. Shiri, M. Chem. Rev. 2012, 112, 3508-3549 10.1021/cr2003954
16. Guo, T.; Huang, F.; Yu, L.; Yu, Z. Tetrahedron Lett. 2015, 56, 296-302 10.1016/j.tetlet.2014.11.114
17. Fischer, E.; Jourdan, F. Ber. Dtsch. Chem. Ges. 1883, 16, 2241-2245 10.1002/cber.188301602141
18. Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 6621-6622 10.1021/ja981045r
19. Köhling, P.; Schmidt, A. M.; Eilbracht, P. Org. Lett. 2003, 5, 3213-3216 10.1021/ol0350184
20. Leogane, O.; Lebel, H. Angew. Chem., Int. Ed. 2008, 47, 350-352 10.1002/anie.200703671
21. Barluenga, J.; Jiménez-Aquino, A.; Aznar, F.; Valdés, C. J. Am. Chem. Soc. 2009, 131, 4031-4041 10.1021/ja808652a
22. Stuart, D. R.; Bertrand-Laperle, M.; Burgess, K. M. N.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 16474-16475 10.1021/ja806955s
23. Shi, Z.; Zhang, C.; Li, S.; Pan, D.; Ding, S.; Cui, Y.; Jiao, N. Angew. Chem., Int. Ed. 2009, 48, 4572-4576 10.1002/anie.200901484
24. Stuart, D. R.; Alsabeh, P.; Kuhn, M.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 18326-18339 10.1021/ja1082624
25. Ackermann, L.; Lygin, A. V. Org. Lett. 2012, 14, 764-767 10.1021/ol203309y
26. Zhang, G.; Yu, H.; Qin, G.; Huang, H. Chem. Commun. 2014, 50, 4331-4334 10.1039/c3cc49751h
27. Shen, D.; Han, J.; Chen, J.; Deng, H.; Shao, M.; Zhang, H.; Cao, W. Org. Lett. 2015, 17, 3283-3285 10.1021/acs.orglett.5b01479
28. Gogoi, A.; Guin, S.; Rout, S. K.; Patel, B. K. Org. Lett. 2013, 15, 1802-1805 10.1021/ol400692b
29. Xia, X.-F.; Zhang, L.-L.; Song, X.-R.; Niu, Y.-N.; Liu, X.-Y.; Liang, Y.-M. Chem. Commun. 2013, 49, 1410-1412 10.1039/c2cc37805a
30. Gogoi, A.; Modi, A.; Guin, S.; Rout, S. K.; Das, D.; Patel, B. K. Chem. Commun. 2014, 50, 10445-10447 10.1039/C4CC04407J
31. Chen, Y.-y.; Chen, J.-h.; Zhang, N.-n.; Ye, L.-m.; Zhang, X.-J.; Yan, M. Tetrahedron Lett. 2015, 56, 478-481 10.1016/j.tetlet.2014.12.002
32. Stokes, B. J.; Liu, S.; Driver, T. G. J. Am. Chem. Soc. 2011, 133, 4702-4705 10.1021/ja111060q
33. Nguyen, Q.; Nguyen, T.; Driver, T. G. J. Am. Chem. Soc. 2013, 135, 620-623 10.1021/ja3113565
34. Kong, C.; Jana, N.; Driver, T. G. Org. Lett. 2013, 15, 824-827 10.1021/ol400137q
35. Jones, C.; Nguyen, Q.; Driver, T. G. Angew. Chem., Int. Ed. 2014, 53, 785-788 10.1002/anie.201308611
36. Alt, I. T.; Plietker, B. Angew. Chem., Int. Ed. 2016, 55, 1519-1522 10.1002/anie.201510045
37. Tan, Y.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 3676-3677 10.1021/ja100676r
38. Nanjo, T.; Tsukano, C.; Takemoto, Y. Org. Lett. 2012, 14, 4270-4273 10.1021/ol302035j
39. Liu, B.; Song, C.; Sun, C.; Zhou, S.; Zhu, J. J. Am. Chem. Soc. 2013, 135, 16625-16631 10.1021/ja408541c
40. Wang, C.; Huang, Y. Org. Lett. 2013, 15, 5294-5297 10.1021/ol402523x
41. Yan, H.; Wang, H.; Li, X.; Xin, X.; Wang, C.; Wan, B. Angew. Chem., Int. Ed. 2015, 54, 10613-10617 10.1002/anie.201503997
42. Deng, G.-B.; Zhang, J.-L.; Liu, Y.-Y.; Liu, B.; Yang, X.-H.; Li, J.-H. Chem. Commun. 2015, 51, 1886-1888 10.1039/C4CC08498E
43. Lerchen, A.; Vásquez-Céspedes, S.; Glorius, F. Angew. Chem., Int. Ed. 2016, 55, 3208-3211 10.1002/anie.201510705
44. Würtz, S.; Rakshit, S.; Neumann, J. J.; Dröge, T.; Glorius, F. Angew. Chem., Int. Ed. 2008, 47, 7230-7233 10.1002/anie.200802482
45. Bernini, R.; Fabrizi, G.; Sferrazza, A.; Cacchi, S. Angew. Chem., Int. Ed. 2009, 48, 8078-8081 10.1002/anie.200902440
46. Yu, W.; Du, Y.; Zhao, K. Org. Lett. 2009, 11, 2417-2420 10.1021/ol900576a
47. Guan, Z.-H.; Yan, Z.-Y.; Ren, Z.-H.; Liu, X.-Y.; Liang, Y.-M. Chem. Commun. 2010, 46, 2823-2825 10.1039/b923971e
48. He, Z.; Liu, W.; Li, Z. Chem.-Asian J. 2011, 6, 1340-1343 10.1002/asia.201100045
49. Neumann, J. J.; Rakshit, S.; Dröge, T.; Würtz, S.; Glorius, F. Chem.-Eur. J. 2011, 17, 7298-7303 10.1002/chem.201100631
50. Shi, Z.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 9220-9222 10.1002/anie.201205079
51. Maity, S.; Zheng, N. Angew. Chem., Int. Ed. 2012, 51, 9562-9566 10.1002/anie.201205137
52. Cai, S.; Yang, K.; Wang, D. Z. Org. Lett. 2014, 16, 2606-2609 10.1021/ol501071k
53. Xia, X.-D.; Xuan, J.; Wang, Q.; Lu, L.-Q.; Chen, J.-R.; Xiao, W.-J. Adv. Synth. Catal. 2014, 356, 2807-2812 10.1002/adsc.201400527
54. Zhang, P.; Xiao, T.; Xiong, S.; Dong, X.; Zhou, L. Org. Lett. 2014, 16, 3264-3267 10.1021/ol501276j
55. Sagadevan, A.; Ragupathi, A.; Hwang, K. C. Angew. Chem., Int. Ed. 2015, 54, 13896-13901 10.1002/anie.201506579
56. Zoller, J.; Fabry, D. C.; Ronge, M. A.; Rueping, M. Angew. Chem., Int. Ed. 2014, 53, 13264-13268 10.1002/anie.201405478
57. Meng, Q.-Y.; Zhong, J.-J.; Liu, Q.; Gao, X.-W.; Zhang, H.-H.; Lei, T.; Li, Z.-J.; Feng, K.; Chen, B.; Tung, C.-H.; Wu, L.-Z. J. Am. Chem. Soc. 2013, 135, 19052-19055 10.1021/ja408486v
58. Zhong, J.-J.; Meng, Q.-Y.; Liu, B.; Li, X.-B.; Gao, X.-W.; Lei, T.; Wu, C.-J.; Li, Z.-J.; Tung, C.-H.; Wu, L.-Z. Org. Lett. 2014, 16, 1988-1991 10.1021/ol500534w
59. Li, X.-B.; Li, Z.-J.; Gao, Y.-J.; Meng, Q.-Y.; Yu, S.; Weiss, R. G.; Tung, C.-H.; Wu, L.-Z. Angew. Chem., Int. Ed. 2014, 53, 2085-2089 10.1002/anie.201310249
60. Zhou, A.-X.; Mao, L.-L.; Wang, G.-W.; Yang, S.-D. Chem. Commun. 2014, 50, 8529-8532 10.1039/C4CC01815J
61. He, R.; Huang, Z.-T.; Zheng, Q.-Y.; Wang, C. Angew. Chem., Int. Ed. 2014, 53, 4950-4953 10.1002/anie.201402575
62. He, K.-H.; Li, Y. ChemSusChem 2014, 7, 2788-2790 10.1002/cssc.201402606
63. Gao, X.-W.; Meng, Q.-Y.; Li, J.-X.; Zhong, J.-J.; Lei, T.; Li, X.-B.; Tung, C.-H.; Wu, L.-Z. ACS Catal. 2015, 5, 2391-2396 10.1021/acscatal.5b00093
64. Zhang, G.; Liu, C.; Yi, H.; Meng, Q.; Bian, C.; Chen, H.; Jian, J.-X.; Wu, L.-Z.; Lei, A. J. Am. Chem. Soc. 2015, 137, 9273-9280 10.1021/jacs.5b05665
65. Xiang, M.; Meng, Q.-Y.; Li, J.-X.; Zheng, Y.-W.; Ye, C.; Li, Z.-J.; Chen, B.; Tung, C.-H.; Wu, L.-Z. Chem.-Eur. J. 2015, 21, 18080-18084 10.1002/chem.201503361
66. Luo, K.; Chen, Y.-Z.; Yang, W.-C.; Zhu, J.; Wu, L. Org. Lett. 2016, 18, 452-455 10.1021/acs.orglett.5b03497
67. Du, P.; Knowles, K.; Eisenberg, R. J. Am. Chem. Soc. 2008, 130, 12576-12577 10.1021/ja804650g
68. Dempsey, J. L.; Brunschwig, B. S.; Winkler, J. R.; Gray, H. B. Acc. Chem. Res. 2009, 42, 1995-2004 10.1021/ar900253e
69. Lazarides, T.; McCormick, T.; Du, P.; Luo, G.; Lindley, B.; Eisenberg, R. J. Am. Chem. Soc. 2009, 131, 9192-9194 10.1021/ja903044n
70. Du, P.; Schneider, J.; Luo, G.; Brennessel, W. W.; Eisenberg, R. Inorg. Chem. 2009, 48, 4952-4962 10.1021/ic900389z
71. Artero, V.; Chavarot-Kerlidou, M.; Fontecave, M. Angew. Chem., Int. Ed. 2011, 50, 7238-7266 10.1002/anie.201007987
72. 00, see: Turro, N. J.; Ramamurthy, V.; Scaiano, J. C. Modern Molecular Photochemistry of Organic Molecules; University Science Books: Sausalito, CA, 2010; p 252.
73. Zhang, Z.-H.; Yin, L.; Wang, Y.-M. Adv. Synth. Catal. 2006, 348, 184-190 10.1002/adsc.200505268