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        Synthesis  2006(7): 1117-1123  
DOI: 10.1055/s-2006-926373
   DOI: 10.1055/s-2006-926373
PAPER
© Georg Thieme Verlag Stuttgart · New YorkPalladium-Catalyzed Cross-Coupling Reactions of Dry Arenediazonium o-Benzenedisulfonimides with Aryltin Compounds
Further Information
            
               
                  
                        
                              Received
                              26 September 2005 
                      
Publication Date:
08 March 2006 (online)
            
         
      
   Publication History
Publication Date:
08 March 2006 (online)

Abstract
The palladium-catalyzed cross-coupling reaction between various arenediazonium o-benzenedisulfonimides and aryltin derivatives is described. The procedure is general, easy and gives pure biaryls in good yields (25 examples, average yield 79%). o-Benzenedisulfonimide can be recovered (>80%) and reused to prepare again the starting material.
Key words
palladium - Stille reaction - cross-coupling - diazonium compounds - sulfur
- Reviews:
- 1a 
             Metal-Catalyzed Cross-Coupling Reactions  
             
            Diederich F.Stang PJ. Wiley-VCH; Weinheim: 1998.Reference Ris Wihthout Link
- 1b 
             
            Geissler H. In Transition Metals for Organic SynthesisBeller M.Bolm C. Wiley-VCH; Weinheim: 1998. Chap. 2.10. p.158-183Reference Ris Wihthout Link
- 1c 
             
            Tsuji J. Transition Metal Reagents and Catalysts Wiley; Chichester U.K.: 2000. Chap. 3. p.27-108Reference Ris Wihthout Link
- Reviews
- 2a 
             
            Hegedus LS. J. Organomet. Chem. 1993, 457: 167Reference Ris Wihthout Link
- 2b 
             
            Kalinin VN. Synthesis 1992, 413Reference Ris Wihthout Link
- 2c 
             
            Bringmann G.Walter R.Weirich R. Angew. Chem., Int. Ed. Engl. 1990, 29: 977Reference Ris Wihthout Link
- 2d 
             
            Snieckus V. Chem. Rev. 1990, 90: 879Reference Ris Wihthout Link
- 2e 
             
            Tsuji J. Palladium Reagents and Catalysts Wiley; Chichester U.K.: 2004. Chap. 3. p.288-348 ; and references thereinReference Ris Wihthout Link
- Reviews:
- 3a 
             
            Hassan J.Sevignon M.Gozzi C.Schulz E.Lemaire M. Chem. Rev. 2002, 102: 1359
- 3b 
             
            Stanforth S. Tetrahedron 1998, 54: 263
- 4a 
             
            Gomberg M.Bachmann WE. J. Am. Chem. Soc. 1924, 46: 2339
- 4b 
             
            Heilbron IM.Hey DH.Cambrest A. J. Chem. Soc. 1940, 1279
- 4c 
             
            Beadle JR.Korzeniowski SH.Rosenberg DE.Garcia-Slenga BJ.Gokel GW. J. Org. Chem. 1984, 49: 1594
- 4d 
             
            Korzeniowski SH.Blum L.Gokel GW. Tetrahedron Lett. 1977, 22: 1871
- Reviews:
- 5a 
             
            Tamao K.Kumada M. In The Chemistry of the Metal-Carbon Bond Vol. 4:Hartley FR. Wiley; New York: 1987. p.820
- 5b 
             
            Sekiya A.Ishikawa N. J. Organomet. Chem. 1976, 118: 349
- 5c 
             
            Negishi E. Acc. Chem. Res. 1982, 15: 340
- 5d 
             
            Erdik E. Tetrahedron 1992, 48: 9577
- 6a 
             
            Miyaura N.Yanagi T.Suzuki A. Synth. Commun. 1981, 513
- 6b 
             
            Miyaura N.Suzuki A. Chem. Rev. 1995, 95: 2457
- 6c 
             
            Martin AR.Yang Y. Acta Chem. Scand. 1993, 47: 221
- 7a 
             
            Millstein D.Stille JK. J. Am. Chem. Soc. 1978, 100: 3636
- 7b 
             
            Millstein D.Stille JK. J. Am. Chem. Soc. 1979, 101: 4981
- 7c 
             
            Stille JK. Angew. Chem., Int. Ed. Engl. 1986, 25: 508
- 7d 
             
            Mitchell TN. Synthesis 1992, 803
- 7e 
             
            Forman FW.Sucholeiki I. J. Org. Chem. 1995, 60: 523
- 7f 
             
            Farina V.Krishnamurthy V.Scott WJ. Org. React. (N.Y.) 1997, 50: 1
- 7g 
             
            Littke AF.Schwarz L.Fu GC. J. Am. Chem. Soc. 2002, 124: 6343
- 8 
             
            Ritter K. Synthesis 1993, 735
- 9a 
             
            Darses S.Tuyet J.Genet J.-P. Tetrahedron Lett. 1996, 37: 3857
- 9b 
             
            Darses S.Tuyet J.Brayer J.-L.Demoute J.-P.Genet J.-P. Bull. Soc. Chim. Fr. 1996, 133: 1095
- 9c 
             
            Sengupta S.Bhattacharyya S. J. Org. Chem. 1997, 62: 3405
- 9d 
             
            Sengupta S.Sadhukhan SK. Tetrahedron Lett. 1998, 39: 715
- 10a 
             
            Kikukawa K.Kono K.Wada F.Matsuda T. Chem. Lett. 1982, 35
- 10b 
             
            Kikukawa K.Umekawa H.Matsuda T. J. Organomet. Chem. 1986, 311: C44
- 10c 
             
            Kikukawa K.Idemoto T.Katayama A.Kono K.Wada F.Matsuda T. J. Chem. Soc., Perkin Trans. 1 1987, 1511
- 10d 
             
            Neumann WP.Wicenec C. Chem. Ber. 1991, 124: 2297
- 10e 
             
            Kang S.-K.Kim J.-S.Choi S.-C.Lim K.-H. Synthesis 1998, 1249
- 11a 
             
            Kikukawa K.Kono K.Wada F.Matsuda T. J. Org. Chem. 1983, 48: 1333 ; and references therein
- 11b 
             
            Bumagin NA.Sukhomlinova LI.Tolstaya TP.Beletskaya IP. Russ. J. Org. Chem. 1994, 30: 1605
- 12 
             
            Barbero M.Degani I.Dughera S.Fochi R. Synthesis 2004, 2386 ; and references therein
- 13 
             
            Sherwood JR.Short WF.Stansfield R. J. Chem. Soc. 1932, 1832
- 14 
             
            Nunez A.Sanchez A.Burgos C.Alvarez-Builla J. Tetrahedron 2004, 60: 6217
- 15 
             
            De Luca G.Renzi G.Cipollini R.Pizzabiocca A. J. Chem. Soc., Perkin Trans. 1 1980, 1901
- 16 
             
            Klement I.Rottlaender M.Tucker CE.Majid TN.Knochel P.Venegas P.Cahiez G. Tetrahedron 1996, 52: 7201
- 17 
             
            Bjorklund C.Nilsson M. Acta Chem. Scand. 1968, 22: 2338
- 18 
             
            Effenberger F.Koch M.Streicher W. Chem. Ber. 1991, 124: 163
- 19 
             
            Idoux JP.Cantwell VS.Nelson SO.Hollier P.Zarrillo R. J. Org. Chem. 1974, 39: 3946
- 20 
             
            Molander GA.Biolatto B. J. Org. Chem. 2003, 68: 4302
- 21 
             
            Beaven GH.Johnson EA. Spectrochim. Acta 1959, 14: 67
- 22 
             
            Nakamura M.Sawasaki K.Okamoto Y.Takamuku S. J. Chem. Soc., Perkin Trans. 1 1994, 141
- 23 
             
            Clennan EL.Mehrsheik-Mohammadi ME. Magn. Reson. Chem. 1985, 23: 985
- 24 
             
            Pelter A.Rowland M.Clements G. Synthesis 1987, 51
- 25 
             
            Xia M.Chen Z.-C. Synth. Commun. 1999, 29: 2457
- 26 
             
            Ohta A.Akita Y.Ohkuwa T.Chiba M.Fukunaga R. Heterocycles 1990, 31: 1951
- 27 
             
            Kolodziuk R.Penciu A.Tollabi M.Framery E.Goux-Henry C.Iourtchenko A.Sinou D. J. Organomet. Chem. 2003, 384
- 28 
             
            Kozyrod RP.Morgan J.Pinhey JT. Aust. J. Chem. 1985, 38: 1147
- 29 
             
            Outten RA.Daves GD. J. Org. Chem. 1989, 54: 29
- 30 
             
            Clarke PI.Howie RA.Wardell JL. J. Inorg. Nucl. Chem. 1974, 36: 2449
- 31 
             
            Azizian H.Eaborn C.Pidcock A. J. Organomet. Chem. 1981, 215: 49
- 32 
             
            Wassmundt FW.Kiesman WF. J. Org. Chem. 1995, 60: 1713
 
    