A first regioselective synthesis of 3-fluoroalkylated benzofurans via palladium-catalyzed annulation of fluorine-containing internal alkynes with variously substituted 2-iodophenol

Tetrahedron

Volumn 60, Issue 51, 2004, Pages 11695-11700

  Konno, Tsutomu ^a   Chae, Jungha ^a   Ishihara, Takashi ^a   Yamanaka, Hiroki ^a  

^a KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Benzofurans; Fluorine

Indexed keywords

ALKYNE DERIVATIVE; BENZOFURAN DERIVATIVE; FLUORINE; PALLADIUM; PHENOL DERIVATIVE;

ANNULATION REACTION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL COMPOSITION; HECK REACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; SYNTHESIS;

EID: 8444238903     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.10.005     Document Type: Article

References (16)

1. For the reviews, see: (a) G. Zeni, and R.C. Larock Chem. Rev. 104 2004 2285 2309
2. I. Nakamura, and Y. Yamamoto Chem. Rev. 104 2004 2127 2198
3. For the precedent work for the syntehsis of fluoroalkylated benzofurans, see: (a) Z.X. Kiang, and F.-L. Qing J. Fluorine Chem. 123 2003 57 60
4. J.S. Kaltenbronn, J. Quin III, B.R. Reisdorph, S. Klutchko, E.E. Reynolds, K.M. Welch, M.A. Flynn, and A.M. Doherty Eur. J. Med. Chem. 32 1997 425 431
5. D.B. Judd, M.D. Dowle, D. Middlemiss, D.I.C. Scopes, B.C. Ross, T.I. Jack, M. Pass, E. Tranquillini, J.E. Hobson, T.A. Panchal, P.G. Stuart, J.M.S. Paton, T. Hubbard, A. Hilditch, G.M. Drew, M.J. Robertson, K.L. Clark, A. Travers, A.A.E. Hunt, J. Polley, P.J. Eddershaw, M.K. Bayliss, G.R. Manchee, M.D. Donnelly, D.G. Walker, and S.A. Richard J. Med. Chem. 37 1994 3108 3120
6. H. Sawada, and M. Nakayama J. Fluroine Chem. 46 1990 423 431
7. J.K. Galllos, P.S. Lianis, and D.N. Nicolaides J. Heterocyclic Chem. 26 1989 1415 1420
8. U. Kuckländer, U. Herweg-Wahl, W. Poll, and L. Rickerich Chem. Ber. 121 1988 1841 1845
9. P.P. Onys'ko, N.V. Proklina, V.P. Prokopenko, and Y.G. Gololobov Zh. Org. Khim. 23 1987 549 552
10. Y. Kobayashi, and I. Kumadaki J. Chem. Soc., Perkin Trans. 1 1980 661 664
11. T. Konno, J. Chae, M. Kanda, G. Nagai, K. Tamura, T. Ishihara, and H. Yamanaka Tetrahedron 59 2003 7571 7580
12. For the annulation reaction of the nonfluorinated substrates, see: R.C. Larock, E.K. Yum, M.J. Doty, and K.K.C. Sham J. Org. Chem. 60 1995 3270 3271
13. The similar addition reaction of phenol to fluorine-containing alkyne has been reported: C.L. Bumgardner, J.E. Bunch, and M.-H. Whangbo Tetrahedron Lett. 27 1986 1883 1886
14. For reviews on the Heck reaction, see: (a) W. Cabri, and I. Candiani Acc. Chem. Res. 28 1995 2 7
15. A. Meijere, and F. Meyer Angew. Chem., Int. Ed. Engl. 33 1994 2379 2411
16. K.J. Edgar, and S.N.J. Falling Org. Chem. 55 1990 5287 5291