Palladium-catalyzed cross-benzannulation of aminoenynes with diynes. Highly regioselective synthesis of polysubstituted anilines

Journal of Organic Chemistry

Volumn 65, Issue 14, 2000, Pages 4338-4341

  Saito, Shinichi ^a   Uchiyama, Naoyuki ^a   Gevorgyan, Vladimir ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; ISOMERISM; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0034647926     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000171m     Document Type: Article

References (19)

1. March, J. Advanced Organic Chemistry; Wiley: New York, 1992; pp 1216-1217.
2. Review: Belfield, A. J.; Brown, G. R.; Foubister, A. J. Tetrahedron 1999, 55, 11399-11428, and references therein.
3. Reviews: (a) Hartwig, J. Synlett 1997, 329-340.
4. (b) Hartwig, J. Angew. Chem., Int. Ed. 1998, 37, 2046-2067.
5. (c) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818.
6. (d) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125-146.
7. Saito, S.; Salter, M. M.; Gevorgyan, V.; Tsuboya, N.; Tando, K.; Yamamoto, Y. J. Am. Chem. Soc. 1996, 118, 3970-3971.
8. (a) Gevorgyan, V.; Takeda, A.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 11313-11314.
9. (b) Gevorgyan, V.; Takeda, A.; Homma, M.; Sadayori, N.; Radhakrishnan, U.; Yamamoto, Y. J. Am. Chem. Soc. 1999, 121, 6391-6402.
10. Reviews: Gevorgyan, V.; Yamamoto, Y. J. Organomet. Chem. 1999, 576, 232-247. Saito, S.; Yamamoto, Y. Chem. Rev., in press.
11. Reviews: Gevorgyan, V.; Yamamoto, Y. J. Organomet. Chem. 1999, 576, 232-247. Saito, S.; Yamamoto, Y. Chem. Rev., in press.
12. (a) Garner, P.; Park, J. M. Organic Syntheses; Wiley: New York, 1998; Collect. Vol. IX, pp 300-305.
13. (b) Garner, P. Tetrahedron Lett. 1984, 25, 5855-5858.
14. The formation of this compound has been briefly mentioned in the literature. See: Reginato, G.; Mordini, A.; Degl'Innocenti, A.; Caracciolo, M. Tetrahedron Lett. 1995, 36, 8275-8278.
15. Trost, B. M.; Sorum, M. T.; Chan, C.; Harms, A. E.; Rühter, G. J. Am. Chem. Soc. 1997, 119, 698-708.
16. Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1998, 37, 7, 489-492.
17. Gevorgyan, V.; Sadayori, N.; Yamamoto, Y. Tetrahedron Lett. 1997, 38, 8603-8604.
18. (a) Wasserman, H. H.; Berger, G. D.; Cho, K. R. Tetrahedron Lett. 1982, 23, 465-468.
19. (b) Rawal, V. H.; Jones, R. J.; Caba, M. P. J. Org. Chem. 1987, 52, 19-28.