A novel synthesis of 2-substituted indole derivatives: A palladium catalyzed cross-coupling reaction of enol triflate derived from N-methyl-2-indolone with (alkenyl)tributylstannane and acetylene

Letters in Organic Chemistry

Volumn 3, Issue 11, 2006, Pages 817-819

  Wada, Akimori ^a   Shinmen, Masaki ^a   Uenishi, Jun'ichi ^b   Ito, Masayoshi ^a  

^a KOBE PHARMACEUTICAL UNIVERSITY   (Japan)

^b KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Acetylene; Alkenyl stannane; Coupling reaction; Enol triflate; Indolone

Indexed keywords

EID: 33845868204     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017806779117030     Document Type: Article

References (13)

1. For review, see; Meijere, A.; de Diederich, F. Metal-Catalyzed Cross-coupling Reactions, Wiley-VCH, Weinheim, 2004.
2. a) Nicolaou, K. C.; Paul B. G.; Sarlah, D. Angew. Chem. Int. Ed. Engl., 2005, 44, 4442;
3. b) Tan, Z.; Negishi, E. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E. Ed.; John Wiley & Sons, Hoboken, 2002; Vol. 1, pp. 863-942.
4. a) Triflate from pyrimidine; Sandosham, J.; Undheim, K.; Rice, F. Heterocycles, 1993, 35, 235
5. b) Triflate from lactam; Larini, P.; Guaruna, A.; Occhito, E. G. Org. Lett., 2006, 8, 781.
6. a) Wada, A.; Nomoto, Y.; Tano, K.; Yamashita, E.; Ito, M. Chem. Pharm. Bull, 2000, 48, 1391
7. b) Wada, A.; Fukunaga, K.; Ito, M. Synlett, 2001, 800;
8. c) Wada, A.; Babu, G.; Shimomoto, S.; Ito, M. Synlett, 2001, 1751.
9. 3) δ: 3.71 (3H, s, NMe), 6.35 (1H, s, ArH), 7.1-7.3 (3H, m, AH), 7.59 (1H, d, J=8 Hz, ArH).
10. Farina, V.; Krishnan, B. J. Am. Chem. Soc., 1991, 113, 9585.
11. 22 O: requires 206.1669, found 206.1667.
12. In the case of trisubstituted olefins 5d and 5e, their stereochemistries were determined after conversion to the corresponding aldehyde by oxidation. see, Wada, A.; Hiraishi, S.; Takamura, N.; Date, T.; Aoe, K.; Ito, M. J. Org. Chem., 1997, 62, 4343.
13. 20O: requires 204.1513, found 204.1520.