Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2006(7): 1117-1123
DOI: 10.1055/s-2006-926373
DOI: 10.1055/s-2006-926373
PAPER
© Georg Thieme Verlag Stuttgart · New York
Palladium-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. -
1b
Geissler H. In Transition Metals for Organic SynthesisBeller M.Bolm C. Wiley-VCH; Weinheim: 1998. Chap. 2.10. p.158-183 -
1c
Tsuji J. Transition Metal Reagents and Catalysts Wiley; Chichester U.K.: 2000. Chap. 3. p.27-108 - Reviews
-
2a
Hegedus LS. J. Organomet. Chem. 1993, 457: 167 -
2b
Kalinin VN. Synthesis 1992, 413 -
2c
Bringmann G.Walter R.Weirich R. Angew. Chem., Int. Ed. Engl. 1990, 29: 977 -
2d
Snieckus V. Chem. Rev. 1990, 90: 879 -
2e
Tsuji J. Palladium Reagents and Catalysts Wiley; Chichester U.K.: 2004. Chap. 3. p.288-348 ; and references therein - 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