RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
Synlett 2004(1): 128-130
DOI: 10.1055/s-2003-44995
DOI: 10.1055/s-2003-44995
LETTER
© Georg Thieme Verlag Stuttgart · New York
l-Proline Promoted Ullmann-Type Coupling Reactions of Aryl Iodides with Indoles, Pyrroles, Imidazoles or Pyrazoles
Weitere Informationen
Received
16 October 2003
Publikationsdatum:
17. Dezember 2003 (online)
Publikationsverlauf
Publikationsdatum:
17. Dezember 2003 (online)
Abstract
The Ullmann-type coupling reactions of aryl iodides and several nitrogen heterocycles occur at 80-90 °C with l-proline as additive, giving N-arylpyrroles, N-arylindoles, N-arylimidazoles, and N-pyrazoles in good to excellent yields.
Key words
cross coupling - nitrogen heterocycles - catalysis - aryl iodide - additive
-
1a
McClenaghan ND.Passalacqua R.Loiseau F.Campagna S.Verheyde B.Hameurlaine A.Dehaen W. J. Am. Chem. Soc. 2003, 125: 5356 -
1b
Paredes E.Kneeteman M.Gonzalez-Sierra M.Mancini PME. Tetrahedron Lett. 2003, 44: 2943 -
1c
Jian H.Tour JM. J. Org. Chem. 2003, 68: 5091 -
1d
Finn J.Mattia K.Morytko M.Ram S.Yang Y.Wu X.Mak E.Gallant P.Keith D. Bioorg. Med. Chem. Lett. 2003, 13: 2231 -
1e
Wang X.Tan J.Zhang L. Org. Lett. 2000, 2: 3107 -
1f
Smith WJ.Sawyer JS. Tetrahedron Lett. 1996, 37: 299 ; and references cited therein - 2
Lindley J. Tetrahedron 1984, 40: 1433 - For recent leading references, see:
-
3a
Yu S.Saenz J.Srirangam K. J. Org. Chem. 2002, 67: 1699 -
3b
Elliott GI.Konopelski JP. Org. Lett. 2000, 2: 3055 -
3c
Collman JP.Zhong MJ. Org. Lett. 2000, 2: 1233 -
3d
Sorenson RJ. J. Org. Chem. 2000, 65: 7747 -
4a
Old DW.Harris MC.Buchwald SL. Org. Lett. 2000, 2: 1403 -
4b
Mann G.Hartwig JF.Driver MS.Fernandez-Rivas C. J. Am. Chem. Soc. 1998, 120: 827 -
5a
Antilla JC.Klapars A.Buchwald SL. J. Am. Chem. Soc. 2002, 124: 11684 -
5b
Klapars A.Antilla JC.Huang X.Buchwald SL. J. Am. Chem. Soc. 2001, 123: 7727 -
6a
Ma D.Zhang Y.Yao J.Wu S.Tao F. J. Am. Chem. Soc. 1998, 120: 12459 -
6b
Ma D.Xia C. Org. Lett. 2001, 3: 2583 -
7a
Ma D.Cai Q.Zhang H. Org. Lett. 2003, 5: 2453 -
7b
Ma D.Cai Q. Org. Lett. 2003, 5: 3799
References
For CuI catalyzed coupling reaction of amides with aryl halides under mild conditions, see ref. [5b] . We are investigating this coupling reaction using our conditions and the results will be reported in due course.