A Novel Pd/Ag-Catalyzed
Sonogashira Coupling Reaction of Terminal Alkynes with
Hypervalent Iodonium Salts

Min Zhu; Zhongshi Zhou; Rui Chen

doi:10.1055/s-2008-1067213

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-00000084.xml

Teilen / Bookmarken

Facebook X Linkedin Weibo

PDF herunterladen

Synthesis 2008(17): 2680-2682
DOI: 10.1055/s-2008-1067213

SHORTPAPER

A Novel Pd/Ag-Catalyzed Sonogashira Coupling Reaction of Terminal Alkynes with Hypervalent Iodonium Salts

Min Zhu*, Zhongshi Zhou, Rui Chen
College of Biological and Environmental Sciences, Zhejiang Shuren University, Hangzhou 310015, Zhejiang, P. R. of China
Fax: +86(571)88297097; e-Mail: hzzm60@163.com;

Weitere Informationen

Publikationsverlauf

Received 13 March 2008
Publikationsdatum:
06. August 2008 (online)

Abstract
Volltext
Referenzen

Lizenzen und Reprints Alle Artikel dieser Rubrik

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

References

1a Diederich F. Stang PJ. Metal-Catalyzed Cross-Coupling Reactions Wiley-VCH; Weinheim: 1998.

Google Scholar
1b Miyaura E. Cross-Coupling Reactions Springer; Berlin: 2002.

Google Scholar
1c Tykwinski RR. Angew. Chem. Int. Ed. 2003, 42: 1566

Google Scholar
2a Paterson I. Davies RDM. Marquez R. Angew. Chem. Int. Ed. 2001, 40: 603

Google Scholar
2b Toyota M. Komori C. Ihara M. J. Org. Chem. 2000, 65: 7110

Google Scholar
2c Ioshimura F. Kawata S. Hirama M. Tetrahedron Lett. 1999, 40: 8281

Google Scholar
2d Nicolaou KC. Dai W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30: 1387

Google Scholar
3a Schumm JS. Pearson DL. Tsur JM. Angew. Chem., Int. Ed. Engl. 1994, 33: 1360

Google Scholar
3b Brunsveld L. Meijer EW. Prince RB. Moore JS. J. Am. Chem. Soc. 2001, 123: 7978

Google Scholar
3c Sonoda M. Inaba A. Itahashi K. Tobe Y. Org. Lett. 2001, 3: 2419

Google Scholar
3d Wong KT. Hsu CC. Org. Lett. 2001, 3: 173

Google Scholar
3e Mongin O. Porres L. Moreaux L. Mertz J. Blanchard-Desce M. Org. Lett. 2002, 4: 719

Google Scholar
4a Glaser C. Ber. Dtsch. Chem. Ges. 1869, 2: 422

Google Scholar
4b Siemsen P. Livingston RC. Diederich F. Angew. Chem. Int. Ed. 2000, 39: 2634

Google Scholar
4c Has AS. J. Org. Chem. 1962, 27: 3320

Google Scholar
4d Rossi R. Carpita A. Bigelli C. Tetrahedron Lett. 1985, 26: 523

Google Scholar
5a Sonogashira K. J. Organomet. Chem. 2002, 653: 46

Google Scholar
5b Negishi E. Anastasia L. Chem. Rev. 2003, 103: 1979

Google Scholar
5c Mori A. Kawashima J. Shimada T. Suguro M. Hirabayashi K. Nishihara Y. Org. Lett. 2000, 2: 2935

Google Scholar
5d Liao M. Fathi R. Yang Z. Org. Lett. 2003, 5: 909

Google Scholar
6a Bertus P. Pale P. J. Organomet. Chem. 1998, 567: 173

Google Scholar
6b Bertus P. Pale P. Tetrahedron Lett. 1996, 37: 2019

Google Scholar
6c Bertus P. Pale P. Tetrahedron Lett. 1997, 38: 8193

Google Scholar
6d Halbes U. Pale P. J. Organomet. Chem. 2003, 687: 420

Google Scholar
6e Halbes U. Pale P. Tetrahedron Lett. 2002, 43: 2039

Google Scholar
6f Halbes U. Vasiliev A. Pale P. Eur. J. Org. Chem. 2005, 2828

Google Scholar
6g Zou G. Zhu J. Tang J. Tetrahedron Lett. 2003, 44: 8709

Google Scholar
7a Zhu M. Song Y.-L. Cao Y. Synthesis 2007, 853

Google Scholar
7b Yan J. Zhou Z.-S. Zhu M. Tetrahedron Lett. 2005, 47: 8173

Google Scholar
7c Yan J. Zhu M. Zhou Z.-S. Eur. J. Org. Chem. 2006, 9: 2060

Google Scholar
7d Yan J. Zhou Z.-S. Zhu M. Chin. Chem. Lett. 2006, 4: 473

Google Scholar
8a Varvoglis A. Tetrahedron 1997, 53: 1179

Google Scholar
8b Stang PJ. Zhdankin VV. Chem. Rev. 1996, 96: 1123

Google Scholar
8c Zhdankin VV. Stang PJ. Chem. Rev. 2002, 102: 2523

Google Scholar
8d Wirth T. Hirt UH. Synthesis 1999, 1271

Google Scholar
8e Kirschning A. Eur. J. Org. Chem. 1998, 11: 2267

Google Scholar
8f Ochiai M. J. Organomet. Chem. 2000, 611: 494

Google Scholar
8g Okuyama T. Acc. Chem. Res. 2002, 35: 12

Google Scholar
8h Zhdankin VV. Stang PJ. Tetrahedron 1998, 54: 10927

Google Scholar
8i Grushin VV. Chem. Soc. Rev. 2000, 29: 315

Google Scholar
9a Bumagin NA. Sukhomlinova LI. Luzikova EV. Tolstaya TP. Beletskaya IP. Tetrahedron Lett. 1996, 37: 897

Google Scholar
9b Kang S.-K. Yoon S.-K. Kim Y.-M. Org. Lett. 2001, 3: 2697

Google Scholar
9c Kang S.-K. Lee H.-W. Jang S.-B. Ho P.-S. J. Chem. Soc., Chem. Commun. 1996, 835

Google Scholar
9d Kang S.-K. Lim K.-H. Ho P.-S. Kim W.-Y. Synthesis 1997, 874

Google Scholar
10 Brandsma L. Verkruijsse HD. Walda B. Synth. Commun. 1991, 21: 137

Crossref Google Scholar
11 Beringer FM. Drexler M. Gindler EM. Lumpkin CC. J. Am. Chem. Soc. 1953, 75: 2705

Crossref Google Scholar
12 Beringer FM. Drexler M. Gindler EM. Lumpkin CC. J. Am. Chem. Soc. 1959, 81: 4321

Google Scholar
13 Margida AJ. Koser GF. J. Org. Chem. 1984, 49: 3643

Crossref Google Scholar
14 Gholap AR. Venkatesan K. Pasricha R. Daniel T. Lahoti RJ. Srinivasan KV. J. Org. Chem. 2005, 70: 4869

Crossref PubMed Google Scholar
15 Katritzky AR. Abdel-Fattah AAA. Wang M. J. Org. Chem. 2002, 67: 7526

Crossref PubMed Google Scholar
16 Liang B. Dai M.-J. Chen J.-H. Yang Z. J. Org. Chem. 2005, 70: 391

Crossref PubMed Google Scholar
17 Mio MJ. Kopel KC. Braun JB. Gadzikwa TL. Hull KL. Brisbois RG. Markworth CJ. Grieco PA. Org. Lett. 2002, 4: 3199

Crossref PubMed Google Scholar
18 Singh R. Just G. J. Org. Chem. 1989, 54: 4453

Crossref Google Scholar