Facile preparation of indoles and 1,2-benzothiazine 1,1-dioxides: Nucleophilic addition of sulfonamides to bromoacetylenes and subsequent palladium-catalyzed cyclization

Angewandte Chemie - International Edition

Volumn 51, Issue 26, 2012, Pages 6471-6474

  Yamagishi, Masahito ^a   Nishigai, Ken ^a   Ishii, Azusa ^a   Hata, Takeshi ^a   Urabe, Hirokazu ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

alkynes; cyclizations; indoles; nucleophilic addition; palladium

Indexed keywords

ALKYNES; BROMINE ATOMS; CYCLIZATIONS; DOUBLE AGENTS; ELECTRON WITHDRAWING GROUP; FACILE PREPARATION; INDOLES; NITROGEN HETEROCYCLES; NUCLEOPHILIC ADDITIONS; PALLADIUM-CATALYZED; TO EFFECT;

ACETYLENE; ADDITION REACTIONS; AMIDES; BROMINE; CATALYSIS; PALLADIUM; SULFUR COMPOUNDS;

CYCLIZATION;

ALKYNE; BROMINE; HETEROCYCLIC COMPOUND; INDOLE DERIVATIVE; OXIDE; PALLADIUM; SULFONAMIDE; THIAZINE DERIVATIVE;

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

ALKYNES; BROMINE; CATALYSIS; CYCLIZATION; HETEROCYCLIC COMPOUNDS; INDOLES; MOLECULAR STRUCTURE; OXIDES; PALLADIUM; SULFONAMIDES; THIAZINES;

EID: 84862673622     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201201024     Document Type: Article

References (75)

1. F. A. Carey, R. J. Sundberg, Advanced Organic Chemistry, 5th ed., Part B, Springer, New York, 2007, pp. 183-200
2. M. B. Smith, J. March, March's Advanced Organic Chemistry, 6th ed., Wiley, Hoboken, 2007, pp. 1130-1132
3. Comprehensive Organic Synthesis, Vol. 4 (Eds.:, B. M. Trost, I. Fleming,), Pergamon, Oxford, 1991.
4. R. D. Chambers, Fluorine in Organic Chemistry, Wiley, New York, 1973
5. S. Tanimoto, R. Taniyasu, T. Takahashi, T. Miyake, M. Okano, Bull. Chem. Soc. Jpn. 1976, 49, 1931-1936
6. A. S. Kende, P. Fludzinski, J. H. Hill, W. Swenson, J. Clardy, J. Am. Chem. Soc. 1984, 106, 3551-3562
7. A. Moyano, F. Charbonnier, A. E. Greene, J. Org. Chem. 1987, 52, 2919-2922
8. L. M. Geary, P. G. Hultin, J. Org. Chem. 2010, 75, 6354-6371.
9. S. I. Miller, J. I. Dickstein, Acc. Chem. Res. 1976, 9, 358-363
10. A. Trofimov, N. Chernyak, V. Gevorgyan, J. Am. Chem. Soc. 2008, 130, 13538-13539.
11. R. D. Chambers, S. R. James, Comprehensive Organic Chemistry, Vol. 1 (Eds.:, D. Barton, W. D. Ollis, J. F. Stoddart,), Pergamon, Oxford, 1979, pp. 557-560
12. G. Himbert, in Methoden der Organischen Chemie (Houben-Weyl), Vol. E15, Part 3 (Eds.:, H. Kropf, E. Schaumann,), Georg Thieme, Stuttgart, 1993, pp. 3319-3329.
13. G. Zweifel, W. Lewis, H. P. On, J. Am. Chem. Soc. 1979, 101, 5101-5102; Halides
14. R. Tanaka, S.-Q. Zhéng, K. Kawaguchi, T. Tanaka, J. Chem. Soc. Perkin Trans. 2 1980, 1714-1720
15. Z. Chen, H. Jiang, Y. Li, C. Qi, Chem. Commun. 2010, 46, 8049-8051; Sulfonamide
16. M. Yamagishi, K. Nishigai, T. Hata, H. Urabe, Org. Lett. 2011, 13, 4873-4875; Imidazoline and Imidazole
17. M. Yamagishi, J. Okazaki, K. Nishigai, T. Hata, H. Urabe, Org. Lett. 2012, 14, 34-37; Addition of thiols was mentioned as an intermediate in the reaction of 1,1-dibromoolefins and a few nucleophiles
18. H. Xu, S. Gu, W. Chen, D. Li, J. Dou, J. Org. Chem. 2011, 76, 2448-2458.
19. V. N. Elokhina, T. I. Yaroshenko, A. S. Nakhmanovich, A. I. Albanov, Russ. J. Org. Chem. 2006, 42, 1866-1867
20. V. N. Elokhina, A. S. Nakhmanovich, L. I. Larina, T. I. Yaroshenko, S. V. Amosova, Russ. J. Org. Chem. 2009, 45, 226-228; With hydroxy group
21. D. Grandjean, P. Pale, J. Chuche, Tetrahedron Lett. 1992, 33, 4905-4908
22. A. S. Nakhmanovich, V. N. Elokhina, L. I. Larina, E. V. Abramova, V. A. Lopyrev, Russ. J. Gen. Chem. 2005, 75, 437-439
23. Z. Miao, M. Xu, B. Hoffmann, B. Bernet, A. Vasella, Helv. Chim. Acta 2005, 88, 1885-1912.
24. B. Das, G. C. Reddy, P. Balasubramanyam, N. Salvanna, Synthesis 2011, 816-820
25. G. A. Burley, D. L. Davies, G. A. Griffith, M. Lee, K. Singh, J. Org. Chem. 2010, 75, 980-983; For a reaction that is proposed to involve silver-catalyzed addition, see
26. Z. Chen, J. Li, H. Jiang, S. Zhu, Y. Li, C. Qi, Org. Lett. 2010, 12, 3262-3265; For intramolecular additions under gold catalysis, see
27. A. K. Buzas, F. M. Istrate, F. Gagosz, Tetrahedron 2009, 65, 1889-1901
28. H. Harkat, A. Y. Dembelé, J.-M. Weibel, A. Blanc, P. Pale, Tetrahedron 2009, 65, 1871-1879
29. A. Buzas, F. Gagosz, Org. Lett. 2006, 8, 515-518; For reviews on relevant metal-mediated hydroamination of acetylenes, see
30. F. Alonso, I. P. Beletskaya, M. Yus, Chem. Rev. 2004, 104, 3079-3159
31. F. Pohlki, S. Doye, Chem. Soc. Rev. 2003, 32, 104-114.
32. Y. Fukudome, H. Naito, T. Hata, H. Urabe, J. Am. Chem. Soc. 2008, 130, 1820-1821
33. H. Naito, T. Hata, H. Urabe, Org. Lett. 2010, 12, 1228-1230
34. Y. Kato, D. H. Yen, Y. Fukudome, T. Hata, H. Urabe, Org. Lett. 2010, 12, 4137-4139.
35. J. Barluenga, C. Valdés, Modern Heterocyclic Chemistry, Vol. 1 (Eds.:, J. Alvarez-Builla, J. J. Vaquero, J. Barluenga,), Wiley-VCH, Weinheim, 2011, pp. 377-531
36. K. Krüger (née Alex), A. Tillack, M. Beller, Adv. Synth. Catal. 2008, 350, 2153-2167
37. G. R. Humphrey, J. T. Kuethe, Chem. Rev. 2006, 106, 2875-2911
38. L. Ackermann, Synlett 2007, 507-526; For recent reports on indole synthesis, see
39. L. Ackermann, A. Althammer, P. Mayer, Synthesis 2009, 3493-3503
40. M. P. Huestis, L. Chan, D. R. Stuart, K. Fagnou, Angew. Chem. 2011, 123, 1374-1377
41. Angew. Chem. Int. Ed. 2011, 50, 1338-1341
42. D. R. Stuart, P. Alsabeh, M. Kuhn, K. Fagnou, J. Am. Chem. Soc. 2010, 132, 18326-18339
43. Z. Shi, C. Zhang, S. Li, D. Pan, S. Ding, Y. Cui, N. Jiao, Angew. Chem. 2009, 121, 4642-4646
44. Angew. Chem. Int. Ed. 2009, 48, 4572-4576
45. A. Wetzel, F. Gagosz, Angew. Chem. 2011, 123, 7492-7496
46. Angew. Chem. Int. Ed. 2011, 50, 7354-7358
47. T. Gehrmann, J. L. Fillol, S. A. Scholl, H. Wadepohl, L. H. Gade, Angew. Chem. 2011, 123, 5876-5881
48. Angew. Chem. Int. Ed. 2011, 50, 5757-5761
49. S. G. Newman, M. Lautens, J. Am. Chem. Soc. 2010, 132, 11416-11417
50. S. Würtz, S. Rakshit, J. J. Neumann, T. Dröge, F. Glorius, Angew. Chem. 2008, 120, 7340-7343
51. Angew. Chem. Int. Ed. 2008, 47, 7230-7233.
52. T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147-1169
53. L. Ackermann, R. Vicente, A. R. Kapdi, Angew. Chem. 2009, 121, 9976-10011
54. Angew. Chem. Int. Ed. 2009, 48, 9792-9826
55. X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem. 2009, 121, 5196-5217
56. Angew. Chem. Int. Ed. 2009, 48, 5094-5115
57. D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174-238; For transition-metal-catalyzed coupling of arene and haloalkenes; see
58. M. Yagoubi, A. C. F. Cruz, P. L. Nichols, R. L. Elliott, M. C. Willis, Angew. Chem. 2010, 122, 8130-8134
59. Angew. Chem. Int. Ed. 2010, 49, 7958-7962
60. M. R. Albicker, N. Cramer, Angew. Chem. 2009, 121, 9303-9306
61. Angew. Chem. Int. Ed. 2009, 48, 9139-9142
62. A. C. F. Cruz, N. D. Miller, M. C. Willis, Org. Lett. 2007, 9, 4391-4393
63. C. C. Hughes, D. Trauner, Angew. Chem. 2002, 114, 1639-1642
64. Angew. Chem. Int. Ed. 2002, 41, 1569-1572
65. L.-C. Campeau, M. Parisien, A. Jean, K. Fagnou, J. Am. Chem. Soc. 2006, 128, 581-590; For a recent review on mechanistic aspects, see
66. L. Ackermann, Chem. Rev. 2011, 111, 1315-1345.
67. D. K. Barange, V. R. Batchu, D. Gorja, V. R. Pattabiraman, L. K. Tatini, J. M. Babu, M. Pal, Tetrahedron 2007, 63, 1775-1789
68. A. Vidal, J.-C. Madelmont, E. Mounetou, Synthesis 2006, 591-593
69. W. J. Layman, Jr., T. D. Greenwood, A. L. Downey, J. F. Wolfe, J. Org. Chem. 2005, 70, 9147-9155
70. H. Zinnes, R. A. Comes, F. R. Zuleski, A. N. Caro, J. Shavel, Jr., J. Org. Chem. 1965, 30, 2241-2246.
71. This synthetic advantage of the products for cyclization was firstly addressed in Ref. [5d]. During the course of our study, a similar method for the preparation of aryl-substituted benzofurans from aromatic haloacetylenes was reported:, S. Wang, P. Li, L. Yu, L. Wang, Org. Lett. 2011, 13, 5968-5971, where aliphatic haloacetylenes appear sluggish substrates.
72. A. Yasuhara, T. Sakamoto, Tetrahedron Lett. 1998, 39, 595-596.
73. X. Zhang, Z. Sui, Tetrahedron Lett. 2003, 44, 3071-3073
74. S. Tumkevicius, V. Masevicius, Synthesis 2007, 3815-3820.
75. To the contrary, mesylation of a mixture of 4 and 5 could provide the N-mesylindoles 4., P. G. M. Wuts, T. W. Greene, Greene's Protective Groups in Organic Synthesis, 4th ed., Wiley, Hoboken, 2007, pp. 873-874.