Novel synthesis of fused indoles and 2-substituted indoles by the palladium-catalyzed cyclization of N-cycloalkenyl-o-haloanilines

Tetrahedron

Volumn 65, Issue 7, 2009, Pages 1327-1335

  Maruyama, Jun ^a   Yamashita, Hiromichi ^a   Watanabe, Takeshi ^a   Arai, Shigeru ^a   Nishida, Atsushi ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

Enamine; Heck reaction; Indole; Olefin isomerization; Palladium

Indexed keywords

ALKENE DERIVATIVE; ANILINE DERIVATIVE; ENAMINE; INDOLE DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; HECK REACTION; ISOMERIZATION; POLYMERIZATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 58149345462     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.12.028     Document Type: Article

References (48)

1. Tsuji J. Palladium Reagents and Catalysts (2003), Wiley, Chichester, UK Chapter 3
2. Link J.T. In: Overman L.E. (Ed). Organic Reactions Vol. 60 (2002), Wiley, New York, NY Chapter 2
3. In: Negishi E. (Ed). Handbook of Organopalladium Chemistry for Organic Synthesis Vols. I and II (2002), Wiley, New York, NY
4. Li J.J., and Gribble G.W. Palladium in Heterocyclic Chemistry (2000), Elsevier, Oxford
5. The pioneering work of the synthesis of indoles using Heck reaction. Mori M., and Ban Y. Tetrahedron Lett. 18 (1977) 1037
6. Synthesis of indoles by intramolecular Heck reaction involving formal 5-endo cyclization of N-alkenyl-o-haloanilines. See:
7. Fuwa H., and Sasaki M. Org. Lett. 9 (2007) 3347
8. Jia J., and Zhu J. J. Org. Chem. 71 (2006) 7826
9. Baran P.S., Hafensteiner B.D., Ambhaikar N.B., Guerrero C.A., and Gallagher J.D. J. Am. Chem. Soc. 128 (2006) 8678
10. Barluenga J., Fernandez M.A., Aznar F., and Valdes C. Chem.-Eur. J. 11 (2005) 2276
11. Lachnace N., April M., and Joly M.-A. Synthesis (2005) 2571
12. Jia Y., and Zhu J. Synlett (2005) 2469
13. Nazaré M., Schneider C., Lindenschmidt A., and Will D.W. Angew. Chem., Int. Ed. 43 (2004) 4526
14. Ackermann L., Kaspar L.T., and Gschrei C.J. Chem. Commun. (2004) 2824
15. Kim G., Kim J.H., Kim W., and Kim Y.A. Tetrahedron Lett. 44 (2003) 8207
16. Yamazaki K., Nakamura Y., and Kondo Y. J. Org. Chem. 68 (2003) 6011
17. Caddick S., and Kofie W. Tetrahedron Lett. 43 (2002) 9347
18. García A., Rodoríguez D., Castedo L., Saá C., and Romínguez D. Tetrahedron Lett. 42 (2001) 1903
19. Michael J.P., de Koning C.B., Petersen R.L., and Stanbury T.V. Tetrahedron Lett. 42 (2001) 7513
20. Edmondson S.D., Mastracchio A., and Parmee E.R. Org. Lett. 2 (2000) 1109
21. Latham E.J., and Stanforth S.P. J. Chem. Soc., Perkin Trans. 1 (1997) 2059
22. Chen C.-y., Lieberman D.R., Larsen R.D., Verhoeven T.R., and Reider P.J. J. Org. Chem. 62 (1997) 2676
23. Blache Y., Sinibaldi-Troin M.-E., Voldoire A., Chavignon O., Gramain J.-C., Teulade J.-C., and Chapat J.-P. J. Org. Chem. 62 (1997) 8553
24. Chen L.C., Yang S.C., and Wang H.M. Synthesis (1995) 385
25. Koerber-Plé K., and Massiot G. Synlett (1994) 759
26. Michael J.P., Chang S.-F., and Wilson C. Tetrahedron Lett. 34 (1993) 8365
27. Sakamoto T., Nagano T., Kondo Y., and Yamanaka H. Synthesis (1990) 215
28. Kasahara A., Izumi T., Murakami S., Yanai H., and Takatori M. Bull. Chem. Soc. Jpn. 59 (1986) 927
29. Iida H., Yuasa Y., and Kibayashi C. J. Org. Chem. 45 (1980) 2938
30. Watanabe T., Arai S., and Nishida A. Synlett (2004) 907
31. Madin A., O'Donnell C.J., Oh T., Old D.W., Overman L.E., and Sharp M.J. J. Am. Chem. Soc. 127 (2005) 18054
32. This crystal structure was deposited at The Cambridge Crystallographic Data Centre, CCDC231397.
33. Sato Y., Watanabe S., and Shibasaki M. Tetrahedron Lett. 33 (1992) 2589
34. Sato Y., Honda T., and Shibasaki M. Tetrahedron Lett. 33 (1992) 2593
35. Sato Y., Nukui S., Sodeoka M., and Shibasaki M. Tetrahedron 50 (1994) 371
36. Molina P., Fresneda P.M., and Almendros P. Tetrahedron 49 (1993) 1223
37. Suzuki H., Thiruvikraman S.V., and Osuka A. Synthesis (1984) 616
38. Vice S.F., Friesen R.W., and Dmitrienko G.I. Tetrahedron Lett. 26 (1985) 165
39. The Heck reaction of tetra-substituted olefins is generally difficult due to steric effects. There are few successful examples. See:
40. Bräse S., Wertal (nee Nüske) H., Frank D., Vidović D., and de Meijere A. Eur. J. Org. Chem. (2005) 4167
41. Meijere A.D., and Bräse S. J. Organomet. Chem. 576 (1999) 88
42. Dankwardtj W., and Flippin L.A. J. Org. Chem. 60 (1995) 2312
43. Grigg R., and Savic V. Chem. Commun. (2000) 873
44. Awang K., Sévenet T., Païs M., and Hadi A.H.A. J. Nat. Prod. 56 (1993) 1134
45. Lapidilectine B (32) has been synthesized. See:
46. Pearson W.H., Mi Y., Lee I.Y., and Stoy P. J. Am. Chem. Soc. 123 (2001) 6724
47. Pearson W.H., Lee I.Y., Mi Y., and Stoy P. J. Org. Chem. 69 (2004) 9109
48. Lennon M., and Proctor G.R. J. Chem. Soc., Perkin Trans. 1 (1979) 2009