Palladium-Catalyzed Regioselective Hydrodebromination of Dibromoindoles: Application to the Enantioselective Synthesis of Indolodioxane U86192A

Journal of Organic Chemistry

Volumn 69, Issue 10, 2004, Pages 3336-3339

  Chae, Junghyun ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; PALLADIUM; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ENANTIOSELECTIVITY; REGIOSELECTIVITY;

BROMINE COMPOUNDS;

4,6 DIBROMOINDOLE; ANTIHYPERTENSIVE AGENT; CARBON; INDOLE DERIVATIVE; INDOLODIOXANE; NITROGEN; OXYGEN; PALLADIUM; PINDOLOL; SEROTONIN; SEROTONIN 1A RECEPTOR; SPIROXATRINE; U 86192A; UNCLASSIFIED DRUG;

ANTIHYPERTENSIVE ACTIVITY; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DEBROMINATION; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; ENANTIOSELECTIVITY; PROTON NUCLEAR MAGNETIC RESONANCE;

ANTIHYPERTENSIVE AGENTS; BROMIDES; BROMINE; CATALYSIS; INDOLES; MOLECULAR STRUCTURE; PALLADIUM; STEREOISOMERISM;

EID: 2442626533     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035819k     Document Type: Article

References (51)

1. (a) Robinson, B. The Fischer Indole Synthesis; John Wiley and Sons: Chichester, 1982.
2. (b) Hughes, D. L. Org. Prep. Proced. Int. 1993, 25, 609.
3. (c) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251.
4. (a) Raffauf, R. F. A Handbook of Alkaloids and Alkaloid-containing Plants; Wiley-Interscience: New York, 1970.
5. (b) Rahman, A. Indole Alkaloids; Harwood Academic Publisher: Amsterdam, 1998.
6. (c) Manske, R. H. F.; Holmes, H. L. The Alkaloids: The Ergot Alkaloids; Academic Press: New York, 1965; Vol. 8, p 725.
7. For reviews on indole syntheses, see: (a) Gribble, G. W. J. Chem. Soc., Perkin Trans. 1 2000, 1045.
8. (b) Sundberg, R. J. Indoles; Academic Press: San Diego, 1996.
9. (a) Madelung, W. Chem. Ber. 1912, 45, 1128.
10. (b) Houlihan, W. J.; Parrino, V. A.; Uike, Y. J. Org. Chem. 1981, 46, 4511.
11. (c) Wacker, D. A.; Kasireddy, P. Tetrahedron Lett. 2002, 43, 5189.
12. (a) Reissert, A. Chem. Ber. 1897, 30, 1030.
13. (b) Izumi, T.; Soutome, M.; Miura, T. J. Heterocycl. Chem. 1992, 29, 1625.
14. (c) Butin, A. V.; Stroganova, T. A.; Lodina, I. V.; Krapivin, G. D. Tetrahedron Lett. 2001, 42, 2031.
15. (a) Leimgruber, W.; Batcho, A. D. Org. Synth. 1985, 63, 214
16. (c) Clark, R. D.; Repke, D. B. Heterocycles 1984, 22, 195.
17. For reviews on metal-catalyzed indole synthesis, see: (a) Hegedus, L. S. Angew. Chem., Int. Ed. 1998. 27, 1113.
18. (b) Larock, R. C. J. Organomet. Chem. 1999, 576. 111.
19. (c) ref. (3).
20. (a) Hegedus, L. S.; Allen, G. F.; Waterman, E. L. J. Am. Chem. Soc. 1976, 98, 2674.
21. (b) Hegedus, L. S.; Allen, G. F.; Bozell, J. J.; Waterman, E. L. J. Am. Chem. Soc. 1978, 100, 5800.
22. (c) Hegedus, L. S.; Allen, G. F.; Olsen, D. J. J. Am. Chem. Soc. 1980, 102, 3583.
23. (a) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689.
24. (b) Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652.
25. Soderberg, B. C.; Schriver, J. A. J. Org. Chem. 1997, 62, 5838.
26. Another approach to prepare 4-substituted indoles involves the direct introduction of a substituent at 4-position via thallation/palladation or lithiation. Both are limited to indoles with specific directing functional groups at the 3-position, however, and use of toxic metals such as thallium detracts from the synthetic utility. Thallation/palladation: (a) Somei, M.; Amari, H.; Makita, Y. Chem. Pharm. Bull. Jpn. 1986, 34, 3971.
27. (b) Somei, M.; Ewasa, E.; Yamada, F. Heterocycles 1986, 24, 3065.
28. Lithiation: (a) Iwao, M. Heterocycles 1993, 36, 29.
29. (b) Chauder, B.; Larkin, A.; Snieckus, V. Org. Lett. 2002, 4, 815.
30. After the methodological portion of this work was complete, two papers that describe the preparation of 4,7- or 5,7-disubstituted indoles from 4,7- or 5,7-dibromoindoles via a selective lithium-bromine exchange reaction appeared. (a) Li, L.; Martins, A. Tetrahedron Lett. 2008, 44, 689.
31. (b) Li, L.; Martins, A. Tetrahedron Lett. 2003, 44, 5987.
32. Wolter, M.; Klapars, A.; Buchwald, S. L. Org. Lett. 2001, 3, 3803.
33. (a) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am Chem. Soc. 1998, 120, 6621.
34. (b) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251.
35. Aryl hydrazines are toxic, corrosive, and prone to redox chemistry as well as radical decomposition, complicating the preparation, storage, and use of these compounds; see: Smith, P. A. S. Derivatives of Hydrazine and the Hydronitrogens Having N-N Bonds, 2nd ed.; The Benjamin/Cummings Publishing Co.: Reading, MA, 1983.
36. Zhao, D.; Hughes, D. L.; Bender D. R.; DeMarco, A. M.; Reider, P. J. J. Org. Chem. 1991, 56, 3001.
37. For regioselective catalytic monodehalogenation of dihaloarenes, see: (a) Page, P. C. B.; Hussain, F.; Bonham, N. M.; Morgan P.; Maggs, J. L.; Park, B. K. Tetrahedron, 1991, 47, 2871.
38. (b) Xie, Y.; Ng, S.; Hor, T. S.; Chan, H. S. O. J. Chem. Res., Synop. 1996, 150.
39. Cortese, N. A.; Heck, R. F. J. Org. Chem. 1977, 42, 3491.
40. Wei, B.; Hor, T. S. J. Mol. Catal. A 1998, 132, 223.
41. Ennis, M. D.; Baze, M. E.; Smith, M. W.; Lawson, C. F.; McCall, R. B.; Lahti, R. A.; Piercey, M. F. J. Med. Chem. 1992, 35, 3058.
42. Kuwabe, S.; Torraca, K. E.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 12202.
43. (a) Crispino, G. A.; Jeong, K.; Kolb, H. C.; Wang, Z.; Xu, D.; Sharpless, K. B. J. Org. Chem. 1993, 58, 3785.
44. (b) Becker, H.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 448.
45. (a) Ready, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 1999, 121, 6086.
46. (b) Ready, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 121, 2687.
47. (c) White, D.; Jacobsen, E. N. Tetrahedron: Asymmetry, in press.
48. The absolute chemistry of 18 was assigned by the analogy to those in ref 22.
49. Fukuyama, T.; Cheung, M.; Jow, C.; Hidai, Y.; Kan, T. Tetrahedron Lett. 1997, 38, 5831.
50. Spectroscopic data for 1 were consistent with that previously reported in ref 19.
51. 2O. See the Supporting Information for details.