Platinum-catalyzed domino reaction with benziodoxole reagents for accessing benzene-alkynylated Indoles

Angewandte Chemie - International Edition

Volumn 54, Issue 18, 2015, Pages 5438-5442

  Li, Yifan ^a   Waser, Jerome ^a  

^a EPFL   (Switzerland)

Author keywords

alkynes; cyclization; heterocycles; hypervalent compounds; platinum

Indexed keywords

AROMATIC COMPOUNDS; BENZENE; CATALYSIS; CATALYSTS; CHEMICAL REACTIONS; IODINE COMPOUNDS; PLATINUM; POTASSIUM COMPOUNDS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

ALKYNES; BIOACTIVE COMPOUNDS; BIOACTIVE MOLECULES; FUNCTIONALIZATIONS; HETEROCYCLES; HYPERVALENT COMPOUNDS; HYPERVALENT IODINE REAGENTS; PLATINUM CATALYSTS;

CYCLIZATION;

2-IODOXYBENZOIC ACID; ALKYNE; INDOLE DERIVATIVE; IODOBENZOIC ACID DERIVATIVE; PLATINUM;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; HYDROGEN BOND; SYNTHESIS;

ALKYNES; CATALYSIS; CYCLIZATION; HYDROGEN BONDING; INDOLES; IODOBENZOATES; MOLECULAR STRUCTURE; PLATINUM;

EID: 84928014939     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201412321     Document Type: Article

References (56)

1. R. J. Sundberg, Indoles, Academic Press, New York, 1996
2. A. F. Pozharskii, A. R. Katritzky, A. T. Soldatenkov, Heterocycles in Life and Society: An Introduction to Heterocyclic Chemistry, Biochemistry and Applications, Chichester, Chichester, 2011.
3. Selected examples
4. B. S. Lane, D. Sames, Org. Lett. 2004, 6, 2897
5. B. S. Lane, M. A. Brown, D. Sames, J. Am. Chem. Soc. 2005, 127, 8050
6. N. P. Grimster, C. Gauntlett, C. R. A. Godfrey, M. J. Gaunt, Angew. Chem. Int. Ed. 2005, 44, 3125
7. Angew. Chem. 2005, 117, 3185
8. R. J. Phipps, N. P. Grimster, M. J. Gaunt, J. Am. Chem. Soc. 2008, 130, 8172
9. N. R. Deprez, D. Kalyani, A. Krause, M. S. Sanford, J. Am. Chem. Soc. 2006, 128, 4972.
10. G. Q. Yang, P. Lindovska, D. J. Zhu, J. Kim, P. Wang, R. Y. Tang, M. Movassaghi, J. Q. Yu, J. Am. Chem. Soc. 2014, 136, 10807
11. H. Liu, C. Zheng, S.-L. You, J. Org. Chem. 2014, 79, 1047.
12. D. W. Robbins, T. A. Boebel, J. F. Hartwig, J. Am. Chem. Soc. 2010, 132, 4068.
13. F. Diederich, P. J. Stang, R. R. Tykwinski, Acetylene Chemistry: Chemistry, Biology and Material Science (Eds.:, F. Diederich, P. J. Stang, R. R. Tykwinski,), Wiley-VCH, Weinheim, 2005.
14. Y. H. Gu, X. M. Wang, Tetrahedron Lett. 2009, 50, 763
15. J. P. Brand, J. Charpentier, J. Waser, Angew. Chem. Int. Ed. 2009, 48, 9346
16. Angew. Chem. 2009, 121, 9510
17. J. P. Brand, C. Chevalley, J. Waser, Beilstein J. Org. Chem. 2011, 7, 565
18. J. P. Brand, C. Chevalley, R. Scopelliti, J. Waser, Chem. Eur. J. 2012, 18, 5655
19. G. L. Tolnai, S. Ganss, J. P. Brand, J. Waser, Org. Lett. 2013, 15, 112
20. T. de Haro, C. Nevado, J. Am. Chem. Soc. 2010, 132, 1512
21. L. Yang, L. A. Zhao, C. J. Li, Chem. Commun. 2010, 46, 4184.
22. M. Elkady, R. Nieß, A. M. Schaible, J. Bauer, S. Luderer, G. Ambrosi, O. Werz, S. A. Laufer, J. Med. Chem. 2012, 55, 8958
23. J. L. Wright, T. F. Gregory, S. R. Kesten, P. A. Boxer, K. A. Serpa, L. T. Meltzer, L. D. Wise, S. A. Espitia, C. S. Konkoy, E. R. Whittemore, R. M. Woodward, J. Med. Chem. 2000, 43, 3408
24. T. Naddo, Y. Che, W. Zhang, K. Balakrishnan, X. Yang, M. Yen, J. Zhao, J. S. Moore, L. Zang, J. Am. Chem. Soc. 2007, 129, 6978.
25. L. F. Tietze, Chem. Rev. 1996, 96, 115.
26. A. Arcadi, S. Cacchi, G. Fabrizi, F. Marinelli, L. M. Parisi, J. Org. Chem. 2005, 70, 6213
27. B. Yao, Q. Wang, J. P. Zhu, Angew. Chem. Int. Ed. 2012, 51, 12311
28. Angew. Chem. 2012, 124, 12477. Review on cascade reactions to access indoles
29. J. Barluenga, F. Rodriguez, F. J. Fananas, Chem. Asian J. 2009, 4, 1036.
30. B. Alcaide, P. Almendros, J. M. Alonso, M. T. Quiros, P. Gadzinski, Adv. Synth. Catal. 2011, 353, 1871
31. A. S. K. Hashmi, W. B. Yang, F. Rominger, Chem. Eur. J. 2012, 18, 6576
32. Y. A. Qiu, W. Q. Kong, C. L. Fu, S. M. Ma, Org. Lett. 2012, 14, 6198.
33. A. Fürstner, P. W. Davies, Angew. Chem. Int. Ed. 2007, 46, 3410
34. Angew. Chem. 2007, 119, 3478
35. A. S. K. Hashmi, Chem. Rev. Chem. Rev 2007, 107, 3180
36. D. J. Gorin, F. D. Toste, Nature 2007, 446, 395.
37. F. M. Beringer, S. A. Galton, J. Org. Chem. 1965, 30, 1930
38. M. Ochiai, T. Ito, Y. Takaoka, Y. Masaki, M. Kunishima, S. Tani, Y. Nagao, J. Chem. Soc. Chem. Commun. 1990, 118
39. V. V. Zhdankin, P. J. Stang, Tetrahedron 1998, 54, 10927.
40. Y. Li, J. P. Brand, J. Waser, Angew. Chem. Int. Ed. 2013, 52, 6743
41. Angew. Chem. 2013, 125, 6875.
42. V. V. Zhdankin, C. J. Kuehl, A. P. Krasutsky, J. T. Bolz, A. J. Simonsen, J. Org. Chem. 1996, 61, 6547.
43. N. Chatani, N. Furukawa, H. Sakurai, S. Murai, Organometallics 1996, 15, 901
44. N. Chatani, K. Kataoka, S. Murai, N. Furukawa, Y. Seki, J. Am. Chem. Soc. 1998, 120, 9104
45. S. I. Lee, N. Chatani, Chem. Commun. 2009, 371
46. A. Fürstner, H. Szillat, B. Gabor, R. Mynott, J. Am. Chem. Soc. 1998, 120, 8305
47. A. Fürstner, H. Szillat, F. Stelzer, J. Am. Chem. Soc. 2000, 122, 6785
48. B. Martín-Matute, D. J. Cárdenas, A. M. Echavarren, Angew. Chem. Int. Ed. 2001, 40, 4754
49. Angew. Chem. 2001, 113, 4890.
50. A. J. Canty, R. P. Watson, S. S. Karpiniec, T. Rodemann, M. G. Gardiner, R. C. Jones, Organometallics 2008, 27, 3203; Selected examples of reaction of platinum-aryl intermediates with alkynes
51. M. E. Cucciolito, A. d. Renzi, G. Roviello, F. Ruffo, Organometallics 2008, 27, 1351
52. J. R. Berenguer, J. Fernández, N. Giménez, E. Lalinde, M. T. Moreno, S. Sánchez, Organometallics 2013, 32, 3943.
53. Y. Qiu, D. Ma, W. Kong, C. Fu, S. Ma, Org. Chem. Frontiers 2014, 1, 62.
54. V. Mamane, P. Hannen, A. Fürstner, Chem. Eur. J. 2004, 10, 4556
55. J. Storch, J. Sykora, J. Cermak, J. Karban, I. Cisarova, A. Ruzicka, J. Org. Chem. 2009, 74, 3090.
56. Y. Shen, C. F. Chen, Chem. Rev. 2012, 112, 1463.