Photoinduced Copper-Catalyzed Regioselective Synthesis of Indoles: Three-Component Coupling of Arylamines, Terminal Alkynes, and Quinones

Angewandte Chemie - International Edition

Volumn 54, Issue 47, 2015, Pages 13896-13901

  Sagadevan, Arunachalam ^a   Ragupathi, Ayyakkannu ^a   Hwang, Kuo Chu ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

annulations; copper; heterocycles; photochemistry; radicals

Indexed keywords

CATALYSIS; COPPER; HYDROCARBONS; LIGHT; PHOTOCHEMICAL REACTIONS;

ANNULATIONS; HETEROCYCLES; RADICALS; REGIOSELECTIVE SYNTHESIS; THREE COMPONENT REACTIONS; THREE-COMPONENT COUPLING; VISIBLE LIGHT INDUCED; VISIBLE-LIGHT IRRADIATION;

REGIOSELECTIVITY;

EID: 84955214540     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201506579     Document Type: Article

References (87)

1. Selected examples:
2. T. Eicher, S. Hauptmann, The Chemistry of Heterocycles: Structure, Reactions, Syntheses, and Applications, 2 nd ed., Wiley-VCH, Weinheim, 2003;
3. J. Alvarez-Builla, J. J. Vaquero, J. Barluenga, Modern Heterocyclic Chemistry, Wiley-VCH, Weinheim, 2011;
4. M. Somei, F. Yamada, Nat. Prod. Rep. 2004, 21, 278-311;
5. M. Shiri, Chem. Rev. 2012, 112, 3508-3549.
6. For selected examples on indole synthesis, see
7. S. Cacchi, G. Fabrizi, Chem. Rev. 2011, 111, 215-283;
8. K. Krüger née Alex, A. Tillack, M. Beller, Adv. Synth. Catal. 2008, 350, 2153-2167;
9. S. Maity, N. Zheng, Angew. Chem. Int. Ed. 2012, 51, 9562-9566;
10. Angew. Chem. 2012, 124, 9700-9704;
11. E. Fischer, F. Jourdan, Ber. Dtsch. Chem. Ges. 1883, 16, 2241-2245, and references therein.
12. R. Chinchilla, C. Nájera, Chem. Rev. 2014, 114, 1783-1826;
13. G. Zeni, R. C. Larock, Chem. Rev. 2006, 106, 4644-4680;
14. R. C. Larock, E. K. Yum, M. D. Refvik, J. Org. Chem. 1998, 63, 7652-7662;
15. B. Lu, Y. Luo, L. Liu, L. Ye, Y. Wang, L. Zhang, Angew. Chem. Int. Ed. 2011, 50, 8358-8362;
16. Angew. Chem. 2011, 123, 8508-8512.
17. L. Ackermann, Acc. Chem. Res. 2014, 47, 281-295;
18. G. Song, F. Wang, X. Li, Chem. Soc. Rev. 2012, 41, 3651-3678.
19. Z. Shi, C. Zhang, S. Li, D. Pan, S. Ding, Y. Cui, N. Jiao, Angew. Chem. Int. Ed. 2009, 48, 4572-4576;
20. Angew. Chem. 2009, 121, 4642-4646;
21. S. Würtz, S. Rakshit, J. J. Neumann, T. Dröge, F. Glorius, Angew. Chem. Int. Ed. 2008, 47, 7230-7233;
22. Angew. Chem. 2008, 120, 7340-7343; [Ru]:
23. L. Ackermann, A. V. Lygin, Org. Lett. 2012, 14, 764-767; [Rh]:
24. D. R. Stuart, P. Alsabeh, M. Kuhn, K. Fagnou, J. Am. Chem. Soc. 2010, 132, 18326-18339; [Au]:
25. S. Cai, K. Yang, D. Z. Wang, Org. Lett. 2014, 16, 2606-2609; [Ni]:
26. W. Song, L. Ackermann, Chem. Commun. 2013, 49, 6638-6640.
27. Y. Wei, H. Zhao, J. Kan, W. Su, M. Hong, J. Am. Chem. Soc. 2010, 132, 2522-2523;
28. M. Shang, H.-L. Wang, S.-Z. Sun, H.-X. Dai, J.-Q. Yu, J. Am. Chem. Soc. 2014, 136, 11590-11593.
29. X.-X. Guo, D.-W. Gu, Z. Wu, W. Zhang, Chem. Rev. 2015, 115, 1622-1651;
30. S. E. Allen, R. R. Walvoord, R. Padilla-Salinas, M. C. Kozlowski, Chem. Rev. 2013, 113, 6234-6458;
31. R. Bernini, G. Fabrizi, A. Sferrazza, S. Cacchi, Angew. Chem. Int. Ed. 2009, 48, 8078-8081;
32. Angew. Chem. 2009, 121, 8222-8225.
33. C. K. Prier, D. A. Rankic, D. W. C. MacMillan, Chem. Rev. 2013, 113, 5322-5363;
34. D. M. Schultz, T. P. Yoon, Science 2014, 343, 985-992;
35. J. M. R. Narayanam, C. R. J. Stephenson, Chem. Soc. Rev. 2011, 40, 102-113;
36. T. P. Yoon, M. A. Ischay, J. Du, Nat. Chem. 2010, 2, 527-532;
37. D. A. Nicewicz, T. M. Nguyen, ACS Catal. 2014, 4, 355-360.
38. M. A. Tasdelen, Y. Yagci, Angew. Chem. Int. Ed. 2013, 52, 5930-5938;
39. Angew. Chem. 2013, 125, 6044-6053;
40. J. A. Brian, T. Youhua, J. K. Christopher, A. D. Cole, S. A. Kristi, N. B. Christopher, Nat. Chem. 2011, 3, 256-259.
41. M. Pirtsch, S. Paria, T. Matsuno, H. Isobe, O. Reiser, Chem. Eur. J. 2012, 18, 7336-7340;
42. A. Baralle, L. Fensterbank, J.-P. Goddard, C. Ollivier, Chem. Eur. J. 2013, 19, 10809-10813;
43. A. C. Hernandez-Perez, S. K. Collins, Angew. Chem. Int. Ed. 2013, 52, 12696-12700;
44. Angew. Chem. 2013, 125, 12928-12932;
45. S. Paria, O. Reiser, ChemCatChem 2014, 6, 2477-2483;
46. D. B. Bagal, G. Kachkovskyi, M. Knorn, T. Rawner, B. M. Bhanage, O. Reiser, Angew. Chem. Int. Ed. 2015, 54, 6999-7002;
47. Angew. Chem. 2015, 127, 7105-7108.
48. S. E. Creutz, K. J. Lotito, G. C. Fu, J. C. Peters, Science 2012, 338, 647-651;
49. A. C. Bissember, R. J. Lundgren, S. E. Creutz, J. C. Peters, G. C. Fu, Angew. Chem. Int. Ed. 2013, 52, 5129-5133;
50. Angew. Chem. 2013, 125, 5233-5237;
51. D. T. Ziegler, J. Choi, J. M. Muñoz-Molina, A. C. Bissember, J. C. Peters, G. C. Fu, J. Am. Chem. Soc. 2013, 135, 13107-13112;
52. C. Uyeda, Y. Tan, G. C. Fu, J. C. Peters, J. Am. Chem. Soc. 2013, 135, 9548-9552;
53. Y. Tan, J. M. Munoz-Molina, G. C. Fu, J. C. Peters, Chem. Sci. 2014, 5, 2831-2835.
54. A. Sagadevan, K. C. Hwang, Adv. Synth. Catal. 2012, 354, 3421-3427;
55. M. Majek, A. Jacobi von Wangelin, Angew. Chem. Int. Ed. 2013, 52, 5919-5921;
56. Angew. Chem. 2013, 125, 6033-6035;
57. A. Sagadevan, A. Ragupathi, K. C. Hwang, Photochem. Photobiol. Sci. 2013, 12, 2110-2118;
58. A. Sagadevan, A. Ragupathi, C.-C. Lin, J. R. Hwu, K. C. Hwang, Green Chem. 2015, 17, 1113-1119.
59. For copper-catalyzed TCC reactions, see:
60. V. A. Peshkov, O. P. Pereshivko, E. V. Van der Eycken, Chem. Soc. Rev. 2012, 41, 3790-3807;
61. N. Chernyak, V. Gevorgyan, Angew. Chem. Int. Ed. 2010, 49, 2743-2746;
62. Angew. Chem. 2010, 122, 2803-2806;
63. C. J. Pierce, M. Nguyen, C. H. Larsen, Angew. Chem. Int. Ed. 2012, 51, 12289-12292;
64. Angew. Chem. 2012, 124, 12455-12458;
65. W. Qian, H. Wang, J. Allen, Angew. Chem. Int. Ed. 2013, 52, 10992-10996;
66. Angew. Chem. 2013, 125, 11198-11202.
67. C. Sambiagio, S. P. Marsden, A. J. Blacker, P. C. McGowan, Chem. Soc. Rev. 2014, 43, 3525-3550;
68. F. Monnier, M. Taillefer, Angew. Chem. Int. Ed. 2009, 48, 6954-6971;
69. Angew. Chem. 2009, 121, 7088-7105.
70. H. Musso, Angew. Chem. Int. Ed. Engl. 1963, 2, 723-735;
71. Angew. Chem. 1963, 75, 965-977.
72. F. Minutolo, M. Macchia, B. S. Katzenellenbogen, J. A. Katzenellenbogen, Med. Res. Rev. 2011, 31, 364-442;
73. "Indole compounds and their use as estrogen agonists/antagonists":, R. Cheswort, U.S. Patent US20030220377A1, November 27, 2003.
74. Initial optimization studies adopted from our previous reported works, see Ref. [12a] and [14d].
75. R. Chinchilla, C. Najera, Chem. Soc. Rev. 2011, 40, 5084-5121.
76. S. D. Koulocheri, S. A. Haroutounian, Eur. J. Org. Chem. 2001, 1723-1729.
77. See the Supporting Information. CCDC 1018306 (4 a), 1018308 (4 k), 1018307 (6 b) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre.
78. See the Supporting Information for the preparation of copper(I) phenylacetylide.
79. R. C. Evans, P. Douglas, C. J. Winscom, Coord. Chem. Rev. 2006, 250, 2093-2126;
80. V. W.-W. Yam, Acc.Chem. Res. 2002, 35, 555-563.
81. M. Yao, H. Senoh, M. Araki, T. Sakai, K. Yasuda, ECS Trans. 2010, 28, 3-10.
82. In situ generated copper(I) phenylacetylide was characterized by IR and UV-visible spectra. See Figures S9 and S10 in the Supporting Information.
83. V. S. Mylnikov, Zh. Strukt. Khim. 1974, 15, 244-249.
84. V. W.-W. Yam, K. K.-W. Lo, K. Man-Chung Wong, J. Organomet. Chem. 1999, 578, 3-30.
85. S. Díez-González, A. Correa, L. Cavallo, S. P. Nolan, Chem. Eur. J. 2006, 12, 7558-7564.
86. G. Zhang, J. Miao, Y. Zhao, H. Ge, Angew. Chem. Int. Ed. 2012, 51, 8318-8321;
87. Angew. Chem. 2012, 124, 8443-8446.