Platinum-Catalyzed Intramolecular Alkylation of Indoles with Unactivated Olefins

Journal of the American Chemical Society

Volumn 126, Issue 12, 2004, Pages 3700-3701

  Liu, Cong ^a   Han, Xiaoqing ^a   Wang, Xiang ^a   Widenhoefer, Ross A ^a  

^a DUKE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CARBOLINE DERIVATIVE; CARBOLINONE DERIVATIVE; INDOLE DERIVATIVE; PLATINUM; PLATINUM COMPLEX; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; ARYLATION; ASYMMETRIC SYNTHESIS; CARBOCYCLIZATION; CATALYSIS; CYCLIZATION; REACTION ANALYSIS; STEREOCHEMISTRY;

ALKENES; ALKYLATION; CATALYSIS; CYCLIZATION; INDOLES; MOLECULAR STRUCTURE; PLATINUM;

EID: 1642281558     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja031814t     Document Type: Article

References (23)

1. Bergman, J.; Pelcman, B. Pure Appl. Chem. 1990, 62, 1967.
2. Cox, E. D.; Cook, J. M. Chem. Rev. 1995, 95, 1797.
3. Saxton, J. E. Nat. Prod. Rep. 1997, 559.
4. Sundberg, R. J. Indoles; Academic Press: San Diego, 1996.
5. Olah, G. A.; Krishnamurti, R.; Prakash, G. K. S. Friedel-Crafts Alkylations. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, pp 293-339.
6. Morrison, G. C.; Waite, R. O.; Serafin, F.; Shavel, J. J. Org. Chem. 1967, 32, 2551.
7. (a) Pei, T.; Widenhoefer, R. A. J. Am. Chem. Soc. 2001, 123, 11290.
8. (b) Pei, T.; Wang, X.; Widenhoefer, R. A. J. Am. Chem. Soc. 2003, 125, 648.
9. (c) Qian, H.; Widenhoefer, R. A. J. Am. Chem. Soc. 2003, 125, 2056.
10. (d) Pei, T.; Widenhoefer, R. A. Chem. Commun. 2002, 650.
11. (e) Wang, X.; Pei, T.; Han, X.; Widenhoefer, R. A. Org. Lett. 2003, 5, 2699.
12. (a) Franzén, J.; Bäckvall, J.-E. J. Am. Chem. Soc. 2003, 125, 6056.
13. (b) Dorange, I.; Löfstedt, J.; Närhi, K.; Franzén, J. Bäckvall, J.-E. Chem. Eur. J. 2003, 9, 3445.
14. For recent reports of the palladium-catalyzed intramolecular oxidative alkylation of indoles with unactivated olefins, see: (a) Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2003, 125, 9578.
15. (b) Abbiati, G.; Beccalli, E. M.; Broggini, G.; Zoni, C. J. Org. Chem. 2003, 68, 7625.
16. Fanizzi, F. P.; Intini, F. P.; Maresca, L.; Natile, G. J. Chem. Soc., Dalton Trans. 1992, 309.
17. See Supporting Information for details concerning optimization.
18. Treatment of 1-methyl-2-(4-methyl-4-pentenyl)indole (Table 1, entry 6) with HCl (30 mol %) in dioxane at 60 °C in the absence of platinum formed no detectable amounts of 4,4,9-trimethyl-2,3,4,9-tetrahydro-1H-carbazole after 24 h.
19. (a) Tan, K. L.; Bergman, R. G.; Ellman. J. A. J. Am. Chem. Soc. 2002, 124, 3202.
20. (b) Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826.
21. (a) Merrifield, J. H.; Fernández, J. M.; Buhro, W. E.; Gladysz, J. A. Inorg. Chem. 1984, 23, 4022.
22. (b) De Luca, N.; Wojcicki, A. J. Organomet. Chem. 1980, 193, 359.
23. 1H NMR spectroscopy (see Supporting Information).