A highly selective tandem cross-coupling of gem-dihaloolefins for a modular, efficient synthesis of highly functionalized indoles

Journal of Organic Chemistry

Volumn 73, Issue 2, 2008, Pages 538-549

  Fang, Yuan Qing ^a   Lautens, Mark ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION; ANILINE; CATALYST ACTIVITY; COPPER; PALLADIUM; SYNTHESIS (CHEMICAL);

ORGANOBORON REAGENTS; SUZUKI COUPLING;

OLEFINS;

ALKENE DERIVATIVE; BORON DERIVATIVE; CARBON; COPPER; INDOLE DERIVATIVE; ORGANOBORON DERIVATIVE; PALLADIUM; ALKENE; ANILINE DERIVATIVE; GEM DIHALOVINYLANILINE; GEM-DIHALOVINYLANILINE; NITROBENZENE DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CHEMICAL BOND; CROSS COUPLING REACTION; MOLECULAR INTERACTION; SUBSTITUTION REACTION; SUZUKI REACTION; SYNTHESIS; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

ALKENES; ANILINE COMPOUNDS; BORON COMPOUNDS; CATALYSIS; INDOLES; MOLECULAR STRUCTURE; NITROBENZENES; PALLADIUM; STEREOISOMERISM;

EID: 40949124680     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701987r     Document Type: Article

References (70)

1. (a) Suzuki, A. J. Organomet. Chem. 2002, 653, 83.
2. (b) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
3. (c) Suzuki, A. in Boronic Acids; Hall, D. G, Ed.; Wiley-VCH: Weinheim, 2005; p 123.
4. (a) Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1978, 100, 3636.
5. (b) Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction; Wiley: New York, 1998.
6. Knochel, P.; Perea, J. J. A.; Jones, P. Tetrahedron 1998, 54, 8275.
7. Hiyama, T.; Shirakawa, E. Top. Curr. Chem. 2002, 219, 62.
8. (a) Muci, A.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
9. (b) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046.
10. (c) Hartwig, J. F. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002; Vol. 1, p 1051.
11. (a) Ramiraz, F.; Desal, N. B.; McKelvie, N. J. Am. Chem. Soc. 1962, 84, 1745.
12. (b) Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 36, 3769.
13. (a) Speziale, A. J.; Marco, G. J.; Ratts, K. W. J. Am. Chem. Soc. 1960, 82, 1260.
14. (b) Speziale, A. J.; Ratts, K. W. J. Am. Chem. Soc. 1962, 84, 854.
15. (c) Speziale, A. J.; Ratts, K. W.; Bissing, D. E. Organic Synthesis; Wiley: New York; Coll. Vol. 5, p 361.
16. Using Grigard or organozinc reagents; (a) Minato, A.; Suzuki, K.; Tamao, K. J. Am. Chem. Soc. 1987, 109, 1257.
17. (b) Minato, A. J. Org. Chem. 1991, 56, 4052.
18. (c) Zeng, X.; Qian, M.; Hu, Q.; Negishi, E. Angew. Chem., Int. Ed. 2004, 43, 2259.
19. (d) Tan, Z.; Negishi, E. Angew. Chem., Int. Ed. 2006, 45, 762.
20. Using organoboron reagents: (e) Roush, W. R.; Mariaty, K. J.; Brown, B. B. Tetrahedron Lett. 1990, 31, 6509.
21. (f) Molander, G. A.; Yokoyama, Y. J. Org. Chem. 2006, 71, 2493.
22. Using organotin: (g) Shen, W.; Wang, L. J. Org. Chem. 1999, 64, 8873.
23. (h) Uenishi, J.; Kawahama, R.; Yonemitsu, O.; Tsuji, J. J. Org. Chem. 1998, 63, 8965.
24. (a) Soderquist, J. A.; Leon, G.; Colberg, J. C.; Martinez, I. Tetrahedron Lett. 1995, 36, 3119.
25. (b) Ma, S.; Xu, B.; Ni, B. J. Org. Chem. 2000, 65, 8532.
26. (c) Ma, S.; Xu, B. J. Org. Chem. 1998, 63, 9156.
27. (a) Wang, L.; Shen, W. Tetrahedron Lett. 1998, 39, 7625.
28. (b) Thielges, S.; Meddah, E.; Bisseret, P.; Eustache, J. Tetrahedron Lett. 2004, 45, 907.
29. Lautens, M.; Fang, Y.-Q. Org. Lett. 2003, 5, 3679.
30. (a) Sundberg, R. J., Ed. Indoles; Academic Press: San Diego, 1996.
31. (b) Gribble, G. W. J. Chem. Soc. Perkin Trans. 1 2000, 1045.
32. (c) Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873.
33. (d) Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875; and references therein.
34. (a) Fang, Y.-Q.; Lautens, M. Org. Lett. 2005, 7, 3549.
35. (b) Lautens, M.; Fang, Y. PCT Int. Appl. WO 06047888. 2006; Chem. Abstr. 2006, 144, 468020.
36. Fayol, A.; Fang, Y.-Q.; Lautens, M. Org. Lett. 2006, 8, 4203.
37. Nagamochi, M.; Fang, Y.-Q.; Lautens, M. Org. Lett. 2007, 9, 2955.
38. Yuen, J.; Fang, Y.-Q.; Lautens, M. Org. Lett. 2006, 8, 653.
39. Fang, Y.-Q.; Yuen, J.; Lautens, M. J. Org. Lett. 2007, 72, 5152.
40. Fang, Y.-Q.; Karisch, R.; Lautens, M. J. Org. Chem. 2007, 72, 1341.
41. Topolski, M. J. Org. Chem. 1995, 60, 5588.
42. (a) Vetelino, M. G.; Coe, J. W. Tetrahedron Lett. 1994, 35, 219.
43. (b) Meshram, H. M.; Ganesh, Y. S. S.; Madhavi, A. V.; Eshwaraiah, B.; Yadav, J. S.; Gunasekar, D. Synth. Commun. 2003, 33, 2497.
44. (c) Makosza, M.; Owczarczyk, Z. J. Org. Chem. 1989, 54, 5094.
45. Crich, D.; Rumthao, S. Tetrahedron 2004, 60, 1513.
46. (a) Baumeister, P.; Blaser, H.-U.; Studer, M. Catal. Lett. 1997, 49, 219.
47. (b) Strem catalogue (2004-2006) number: 78-1512.
48. Kobrich, G.; Trapp, H.; Akhtar, A. Chem. Ber. 1968, 101, 264.
49. Olah, G. A.; Yamada, Y. J. Org. Chem. 1975, 40, 1107.
50. Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553.
51. (a) Walker, S. D.; Barder, T. E.; Martinelli, J. R.; Buchwald, S. L. Angew. Chem., Int. Ed. 2004, 43, 1871.
52. (b) Barder, T. E.; Buchwald, S. L. Org. Lett. 2004, 6, 2649.
53. (c) Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685.
54. (d) Billingsley, K. L.; Anderson, K. W.; Buchwald, S. L. Angew. Chem., Int. Ed. 2006, 45, 3484.
55. Miyaura, N.; Satoh, M.; Suzuki, A. Tetrahedron Lett. 1986, 27, 3745.
56. (a) Hu, W.; Guo, Z.; Chu, F.; Bai, A.; Yi, X.; Cheng, G.; Li, J. Bioorg. Med. Chem. 2003, 11, 1153.
57. (b) Guo, Z.; Cheng, G.; Chu; F. (P. R. China). U.S. Pat. Appl. Publ. US 2004058977; Chem. Abstr. 2004, 140, 270734.
58. (c) Liu, Y.; Gribble, G. W. Tetrahedron Lett. 2000, 41, 8717.
59. Reddy, T. J.; Leclair, M.; Proulx, M. Synlett 2005, 583.
60. Gungor, T.; Teulon, J.-M. (Laboratoires UPSA, Fr.), WO 9,805,-639, 1998; Chem. Abstr. 1998, 128, 180330.
61. (a) Von Angerer, E.; Strohmeier, J. J. Med. Chem. 1987, 30, 131.
62. (b) Von Angerer, E.; Biberger, C.; Schneider, M. (Schering A.-G., Germany), WO 9,603,375, 1996; Chem. Abstr. 1996, 125, 33474.
63. Lin, T.-s. (Lightronik Technology Inc., Taiwan), US 6,790,539, 2004; Chem. Abstr. 2004, 140, 136161.
64. Chan, D. M. T.; Lam, P. Y. S. In Boronic Acids; Hall, D. G., Eds.; Wiley-VCH: Weinheim, 2005; p 205.
65. Quach, T. D.; Batey, R. A. Org. Lett. 2003, 5, 4397.
66. Antilla, J. C.; Buchwald, S. L. Org. Lett. 2001, 3, 2077.
67. Bergman, J.; Venemalm, L. J. Org. Chem. 1992, 57, 2495.
68. (a) Kudo, K.; Hidai, M.; Murayama, T.; Uchida, Y. J. Chem. Soc., Chem. Commun. 1970, 1701-1702.
69. (b) Leoni, P.; Sommovigo, M.; Pasquali, M.; Midollini, S.; Braga, D.; Sabatino, P. Organometallics 1991, 10, 1038.
70. Hay, A. S.; Paventi, M. PCT Int. Appl. WO 9309079, 1993.