Palladium-catalyzed aminobenzannulation during Sonogashira couplings using o-bromoacetophenone

Journal of Organometallic Chemistry

Volumn 634, Issue 1, 2001, Pages 1-4

  Herndon, James W ^a   Zhang, Yanshi ^a   Wang, Ke ^a  

^a NEW MEXICO STATE UNIVERSITY   (United States)

Author keywords

Alkynylation; Aminonaphthalenes; Benzannulation; Cyclization; Cycloaddition; O Bromoacetophenone; Palladium catalysis; Sonogashira coupling

Indexed keywords

EID: 0002121207     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(01)01104-4     Document Type: Article

References (20)

1. Jiang D., Herndon J.W. Org. Lett. 2:2000;1267.
2. Reaction of alkynes with o-iodoacetophenone and related compounds provides derivatives of 2 with no problems. (a) K. Maeyama, N. Iwasawa, J. Am. Chem. Soc. 120 (1998) 1928;
3. (b) N. Iwasawa, M. Shido, K. Maeyama, H. Kusama, J. Am. Chem. Soc. 122 (2000) 10226;
4. © J.D. Tovar, T.M. Swager, J. Org. Chem. 64 (1999) 6499.
5. Makra F., Rohloff J.C., Muehldorf A.V., Link J.O. Tetrahedron Lett. 36:1995;6815.
6. Ciufolini M.A., Weiss T.J. Tetrahedron Lett. 35:1994;1127.
7. Merlic C.A., Aldrich C.C., Albaneze-Walker J., Saghatelian A., Mammen J. J. Org. Chem. 66:2001;1297.
8. Merlic C.A., Xu D., Gladstone B.G. J. Org. Chem. 58:1993;538.
9. Merlic C.A., Burns E.E., Xu D., Chen S.Y. J. Am. Chem. Soc. 114:1992;8722.
10. Rahm A., Wulff W.D. J. Am. Chem. Soc. 118:1996;1807.
11. Grotjahn D.B., Dötz K.H. Synlett. 1991;381.
12. Grotjahn D.B., Kroll F.E.K., Schaefer T., Harms K., Dötz K.K. Organometallics. 11:1992;298.
13. Dötz K.H., Grotjahn D.B., Harms K. Angew. Chem. Int. Ed. 28:1989;1384.
14. Dötz K.H., Kroll F., Harms K. J. Organomet. Chem. 459:1993;169.
15. Barluenga J., López S., Martinez S., Tomás M. J. Org. Chem. 63:1998;7588.
16. Hsung R.P., Wulff W.D., Chamberlin S., Liu Y., Liu R., Wang H., Quinn J.F., Wang S.L.B., Rheingold A.L. Synthesis. 2001;200.
17. Wulff W.D., Gilbert A.M., Hsung R.P., Rahm A. J. Org. Chem. 60:1995;4566.
18. Anderson B.A., Wulff W.D., Rheingold A.L. J. Am. Chem. Soc. 112:1990;8615.
19. Merino I., Hegedus L.S. Organometallics. 14:1995;2522.
20. Similar intramolecular nucleophilic addition processes have been proposed in palladium-catalyzed approaches to benzofurans and indoles. R.C. Larock, J. Organomet. Chem. 576 (1999) 111.