GaCl3-Catalyzed ortho-ethynylation reaction of N-benzylanilines

Tetrahedron Letters

Volumn 45, Issue 22, 2004, Pages 4333-4335

  Amemiya, Ryo ^a   Fujii, Akiko ^a   Yamaguchi, Masahiko ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Catalysis; Chloroethyne; Gallium(III) chloride; N Benzylaniline; ortho Ethynylation

Indexed keywords

ANILINE DERIVATIVE; GALLIUM CHLORIDE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION; CONFORMATIONAL TRANSITION; METHYLATION; REACTION ANALYSIS; SILYLATION;

EID: 2342497222     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.03.187     Document Type: Article

References (16)

1. Hiroya K., Itoh S., Ozawa M., Kanamori Y., Sakamoto T. Tetrahedron Lett. 43:2002;1277
2. McDonald F.E., Chatterjee A.K. Tetrahedron Lett. 38:1997;7687
3. Ezquerra J., Pedregal C., Lamas C. J. Org. Chem. 61:1996;5804. also see references cited therein
4. Sakamoto T., Konodo Y., Yamanaka H. Heterocycles. 24:1986;31
5. Rudisill D.E., Stille J.K. J. Org. Chem. 54:1989;5856
6. Taylor E.C., Kats A.H., Salgado-Zamora H. Tetrahedron Lett. 26:1985;5963
7. Talyor E.C., Katz A.H., Alvarado S.I., McKillop A. J. Organomet. Chem. 285:1985;C9
8. Fujiwara J., Fukutani Y., Sano H., Maruoka K., Yamamoto H. J. Am. Chem. Soc. 105:1983;7177
9. Yamaguchi M., Arisawa M., Hirama M. Chem. Commun. 1998;1399
10. Kobayashi K., Arisawa M., Yamaguchi M. J. Am. Chem. Soc. 124:2002;8528
11. See the followings for the ethynylation reaction of gallium enolates. Arisawa M., Amemiya R., Yamaguchi M. Org. Lett. 4:2002;2209
12. Amemiya R., Fujii A., Arisawa M., Yamaguchi M. Chem. Lett. 32:2003;298
13. Amemiya R., Fujii A., Arisawa M., Yamaguchi M. J. Organomet. Chem. 686:2003;94
14. Kanetani F., Okada E., Neguro K. Bull. Chem. Soc. Jpn. 59:1986;2517
15. 27NSi: 321.1913. Found: 321.1890
16. 4, and concentrated. The residue was purified by flash column chromatography (hexane/ethyl acetate = 100/3) to give 10 (94 mg, 58%)