Efficient carbazole synthesis via Pd/Cu-cocatalyzed cross-coupling/ isomerization of 2-allyl-3-iodoindoles and terminal alkynes

Organic Letters

Volumn 16, Issue 6, 2014, Pages 1542-1545

  Zhu, Can ^a   Ma, Shengming ^a,b  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b EAST CHINA NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; CARBAZOLE DERIVATIVE; COPPER; INDOLE DERIVATIVE; IODINATED HYDROCARBON; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; ISOMERISM; SYNTHESIS;

ALKYNES; CARBAZOLES; CATALYSIS; COPPER; CYCLIZATION; HYDROCARBONS, IODINATED; INDOLES; ISOMERISM; MOLECULAR STRUCTURE; PALLADIUM;

EID: 84896991258     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol500119r     Document Type: Article

References (56)

1. Kapil, R. S. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1971; Vol. 13, p 273.
2. Husson, H. P. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1985; Vol. 26, p 1.
3. Gallagher, P. T. In Science of Synthesis; Thomas, E. J., Ed.; Thieme: Stuttgart, 2001; Vol. 10, p 693.
4. Knölker, H.-J. Curr. Org. Synth. 2004, 1, 309
5. Knölker, H.-J. Chem. Lett. 2009, 38, 8
6. Knölker, H.-J. Chem. Soc. Rev. 1999, 28, 151
7. Kong, W.; Fu, C.; Ma, S. Chem.-Eur. J. 2011, 17, 13134
8. Qiu, Y.; Ma, D.; Fu, C.; Ma, S. Org. Biomol. Chem. 2013, 11, 1666
9. Bauer, I.; Knölker, H.-J. Top. Curr. Chem. 2012, 309, 203
10. Wang, Y. Z.; Epstein, A. J. Acc. Chem. Res. 1999, 32, 217
11. O'Brien, D. F.; Burrows, P. E.; Forrest, S. R.; Koene, B. E.; Loy, D. E.; Thompson, M. E. Adv. Mater. 1998, 10, 1108
12. Thomas, J. K. R.; Lin, J. T.; Tao, Y.-T.; Ko, C.-W. J. Am. Chem. Soc. 2001, 123, 9404
13. Huang, J.; Niu, Y.; Yang, W.; Mo, Y.; Yuan, M.; Cao, Y. Macromolecules 2002, 35, 6080
14. Sanda, F.; Nakai, T.; Kobayashi, N.; Masuda, T. Macromolecules 2004, 37, 2703
15. Häussler, M.; Liu, J.; Zheng, R.; Lam, J. W. Y.; Qin, A.; Tang, B. Z. Macromolecules 2007, 40, 1914
16. Knölker, H.-J.; Reddy, K. R. Chem. Rev. 2002, 102, 4303
17. Schmidt, A. W.; Reddy, K. R.; Knölker, H.-J. Chem. Rev. 2012, 112, 3193
18. Kong, W.; Fu, C.; Ma, S. Chem. Commun. 2009, 4572
19. Qiu, Y.; Kong, W.; Fu, C.; Ma, S. Org. Lett. 2012, 14, 6198
20. Ackermann, L.; Althammer, A. Angew. Chem., Int. Ed. 2007, 46, 1627
21. Lim, B.-Y.; Choi, M.-K.; Cho, C.-G. Tetrahedron Lett. 2011, 52, 6015
22. Hernandez-Perez, A. C.; Collins, S. K. Angew. Chem., Int. Ed. 2013, 52, 12696
23. Tsang, W. C. P.; Zheng, N.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 14560
24. Forke, R.; Jäger, A.; Knölker, H.-J. Org. Biomol. Chem. 2008, 6, 2481
25. Gruner, K. K.; Knölker, H.-J. Org. Biomol. Chem. 2008, 6, 3902
26. Knott, K. E.; Auschill, S.; Jäger, A.; Knölker, H.-J. Chem. Commun. 2009, 1467
27. Kumar, V. P.; Gruner, K. K.; Kataeva, O.; Knölker, H.-J. Angew. Chem., Int. Ed. 2013, 52, 11073
28. Shu, D.; Winston-McPherson, G. N.; Song, W.; Tang, W. Org. Lett. 2013, 15, 4162
29. Tu, S.; Ding, C.; Hu, W.; Li, F.; Yao, Q.; Zhang, A. Mol. Divers. 2011, 15, 91
30. Ozaki, K.; Zhang, H.; Ito, H.; Lei, A.; Itami, K. Chem. Sci 2013, 4, 3416
31. Wasilke, J.-C.; Obrey, S. J.; Baker, R. T.; Bazan, G. C. Chem. Rev. 2005, 105, 1001
32. Denmark, S. E.; Thorarensen, A. Chem. Rev. 1996, 96, 137
33. Guo, H.-C.; Ma, J.-A. Angew. Chem., Int. Ed. 2006, 45, 354
34. Loh, C. C. J.; Atodiresei, I.; Enders, D. Chem.-Eur. J. 2013, 19, 10822
35. Kanbayashi, N.; Takenaka, K.; Okamura, T.-a.; Onitsuka, K. Angew. Chem., Int. Ed. 2013, 52, 4897
36. Liu, T.-P.; Xing, C.-H.; Hu, Q.-S. Angew. Chem., Int. Ed. 2010, 49, 2909
37. Jia, Z.-X.; Luo, Y.-C.; Wang, Y.; Chen, L.; Xu, P.-F.; Wang, B. Chem.-Eur. J. 2012, 18, 12958
38. Cai, Q.; Liang, X.-W.; Wang, S.-G.; Zhang, J.-W.; Zhang, X.; You, S.-L. Org. Lett. 2012, 14, 5022
39. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457
40. Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079
41. Roesch, K. R.; Larock, R. C. Org. Lett. 1999, 1, 553
42. Yue, D.; Larock, R. C. J. Org. Chem. 2002, 67, 1905
43. Roesch, K. R.; Larock, R. C. J. Org. Chem. 2002, 67, 86
44. Zhu, C.; Ma, S. Org. Lett. 2013, 15, 2782
45. Kim, H.; Lee, K.; Kim, S.; Lee, P. H. Chem. Commun. 2010, 46, 6341
46. Zhu, C.; Zhang, X.; Lian, X.; Ma, S. Angew. Chem., Int. Ed. 2012, 51, 7817
47. 3, T = 293(2) K, Z = 4, reflections collected/unique: 13011/4813 (R (int) = 0.0240), no. of observations [>2 (I)] 4318; parameter: 326. Supplementary crystallographic data have been deposited with the Cambridge Crystallographic Data Centre. CCDC 979538 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
48. 3, T = 293(2) K, Z = 4, reflections collected/unique: 8407/3231 (R (int) = 0.0208), no. of observations [>2(I)] 2629; parameter: 219. Supplementary crystallographic data have been deposited at the Cambridge Crystallographic Data Centre. CCDC 979539 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
49. MacKay, J. A.; Bishop, R. L.; Rawal, V. H. Org. Lett. 2005, 7, 3421
50. Chinchilla, R.; Nájera, C. Chem. Rev. 2007, 107, 874
51. Köllhofer, A.; Plenio, H. Chem.-Eur. J. 2003, 9, 1416
52. Doucet, H.; Hierso, J.-C. Angew. Chem., Int. Ed. 2007, 46, 834
53. Lamblin, M.; Nassar-Hardy, L.; Hierso, J.-C.; Fouquet, E.; Felpin, F.-X. Adv. Synth. Catal. 2010, 352, 33
54. Chinchilla, R.; Nájera, C. Chem. Soc. Rev. 2011, 40, 5084
55. Torborg, C.; Huang, J.; Schulz, T.; Schäffner, B.; Zapf, A.; Spannenberg, A.; Börner, A.; Beller, M. Chem.-Eur. J. 2009, 15, 1329
56. Zhao, G.; Zhang, Q.; Zhou, H. Adv. Synth. Catal. 2013, 355, 3492