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        Synlett  2004(1): 128-130  
DOI: 10.1055/s-2003-44995
   DOI: 10.1055/s-2003-44995
LETTER
© Georg Thieme Verlag Stuttgart · New Yorkl-Proline Promoted Ullmann-Type Coupling Reactions of Aryl Iodides with Indoles, Pyrroles, Imidazoles or Pyrazoles
Further Information
            
               
                  
                        
                              Received
                              16 October 2003 
                      
Publication Date:
17 December 2003 (online)
            
         
      
   Publication History
Publication Date:
17 December 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: 12459Reference Ris Wihthout Link
- 6b 
             
            Ma D.Xia C. Org. Lett. 2001, 3: 2583Reference Ris Wihthout Link
- 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.
 
    