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 2008(17): 2680-2682
DOI: 10.1055/s-2008-1067213
DOI: 10.1055/s-2008-1067213
SHORTPAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkA Novel Pd/Ag-Catalyzed Sonogashira Coupling Reaction of Terminal Alkynes with Hypervalent Iodonium Salts
Further Information
Received
13 March 2008
Publication Date:
06 August 2008 (online)
Publication History
Publication Date:
06 August 2008 (online)

Abstract
A novel and fast Sonogashira coupling reaction of terminal alkynes with hypervalent iodonium salts was achieved in the presence of catalytic amount of palladium chloride and silver(I) iodide, providing a convenient method for the synthesis of arylalkynes in good yields in a short time.
Key words
Sonogashira reaction - terminal alkynes - hypervalent iodonium salts - Pd/Ag catalyst
- 1a
Diederich F.Stang PJ. Metal-Catalyzed Cross-Coupling Reactions Wiley-VCH; Weinheim: 1998. - 1b
Miyaura E. Cross-Coupling Reactions Springer; Berlin: 2002. - 1c
Tykwinski RR. Angew. Chem. Int. Ed. 2003, 42: 1566 - 2a
Paterson I.Davies RDM.Marquez R. Angew. Chem. Int. Ed. 2001, 40: 603 - 2b
Toyota M.Komori C.Ihara M. J. Org. Chem. 2000, 65: 7110 - 2c
Ioshimura F.Kawata S.Hirama M. Tetrahedron Lett. 1999, 40: 8281 - 2d
Nicolaou KC.Dai W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30: 1387 - 3a
Schumm JS.Pearson DL.Tsur JM. Angew. Chem., Int. Ed. Engl. 1994, 33: 1360 - 3b
Brunsveld L.Meijer EW.Prince RB.Moore JS. J. Am. Chem. Soc. 2001, 123: 7978 - 3c
Sonoda M.Inaba A.Itahashi K.Tobe Y. Org. Lett. 2001, 3: 2419 - 3d
Wong KT.Hsu CC. Org. Lett. 2001, 3: 173 - 3e
Mongin O.Porres L.Moreaux L.Mertz J.Blanchard-Desce M. Org. Lett. 2002, 4: 719 - 4a
Glaser C. Ber. Dtsch. Chem. Ges. 1869, 2: 422 - 4b
Siemsen P.Livingston RC.Diederich F. Angew. Chem. Int. Ed. 2000, 39: 2634 - 4c
Has AS. J. Org. Chem. 1962, 27: 3320 - 4d
Rossi R.Carpita A.Bigelli C. Tetrahedron Lett. 1985, 26: 523 - 5a
Sonogashira K. J. Organomet. Chem. 2002, 653: 46 - 5b
Negishi E.Anastasia L. Chem. Rev. 2003, 103: 1979 - 5c
Mori A.Kawashima J.Shimada T.Suguro M.Hirabayashi K.Nishihara Y. Org. Lett. 2000, 2: 2935 - 5d
Liao M.Fathi R.Yang Z. Org. Lett. 2003, 5: 909 - 6a
Bertus P.Pale P. J. Organomet. Chem. 1998, 567: 173 - 6b
Bertus P.Pale P. Tetrahedron Lett. 1996, 37: 2019 - 6c
Bertus P.Pale P. Tetrahedron Lett. 1997, 38: 8193 - 6d
Halbes U.Pale P. J. Organomet. Chem. 2003, 687: 420 - 6e
Halbes U.Pale P. Tetrahedron Lett. 2002, 43: 2039 - 6f
Halbes U.Vasiliev A.Pale P. Eur. J. Org. Chem. 2005, 2828 - 6g
Zou G.Zhu J.Tang J. Tetrahedron Lett. 2003, 44: 8709 - 7a
Zhu M.Song Y.-L.Cao Y. Synthesis 2007, 853 - 7b
Yan J.Zhou Z.-S.Zhu M. Tetrahedron Lett. 2005, 47: 8173 - 7c
Yan J.Zhu M.Zhou Z.-S. Eur. J. Org. Chem. 2006, 9: 2060 - 7d
Yan J.Zhou Z.-S.Zhu M. Chin. Chem. Lett. 2006, 4: 473 - 8a
Varvoglis A. Tetrahedron 1997, 53: 1179 - 8b
Stang PJ.Zhdankin VV. Chem. Rev. 1996, 96: 1123 - 8c
Zhdankin VV.Stang PJ. Chem. Rev. 2002, 102: 2523 - 8d
Wirth T.Hirt UH. Synthesis 1999, 1271 - 8e
Kirschning A. Eur. J. Org. Chem. 1998, 11: 2267 - 8f
Ochiai M. J. Organomet. Chem. 2000, 611: 494 - 8g
Okuyama T. Acc. Chem. Res. 2002, 35: 12 - 8h
Zhdankin VV.Stang PJ. Tetrahedron 1998, 54: 10927 - 8i
Grushin VV. Chem. Soc. Rev. 2000, 29: 315 - 9a
Bumagin NA.Sukhomlinova LI.Luzikova EV.Tolstaya TP.Beletskaya IP. Tetrahedron Lett. 1996, 37: 897 - 9b
Kang S.-K.Yoon S.-K.Kim Y.-M. Org. Lett. 2001, 3: 2697 - 9c
Kang S.-K.Lee H.-W.Jang S.-B.Ho P.-S. J. Chem. Soc., Chem. Commun. 1996, 835 - 9d
Kang S.-K.Lim K.-H.Ho P.-S.Kim W.-Y. Synthesis 1997, 874 - 10
Brandsma L.Verkruijsse HD.Walda B. Synth. Commun. 1991, 21: 137 - 11
Beringer FM.Drexler M.Gindler EM.Lumpkin CC. J. Am. Chem. Soc. 1953, 75: 2705 - 12
Beringer FM.Drexler M.Gindler EM.Lumpkin CC. J. Am. Chem. Soc. 1959, 81: 4321 - 13
Margida AJ.Koser GF. J. Org. Chem. 1984, 49: 3643 - 14
Gholap AR.Venkatesan K.Pasricha R.Daniel T.Lahoti RJ.Srinivasan KV. J. Org. Chem. 2005, 70: 4869 - 15
Katritzky AR.Abdel-Fattah AAA.Wang M. J. Org. Chem. 2002, 67: 7526 - 16
Liang B.Dai M.-J.Chen J.-H.Yang Z. J. Org. Chem. 2005, 70: 391 - 17
Mio MJ.Kopel KC.Braun JB.Gadzikwa TL.Hull KL.Brisbois RG.Markworth CJ.Grieco PA. Org. Lett. 2002, 4: 3199 - 18
Singh R.Just G. J. Org. Chem. 1989, 54: 4453