Electrochemical generation of silver acetylides from terminal alkynes with a Ag anode and integration into sequential Pd-catalysed coupling with arylboronic acids

Chemical Communications

Volumn 46, Issue 48, 2010, Pages 9256-9258

  Mitsudo, Koichi ^a   Shiraga, Takuya ^a   Mizukawa, Jun Ichi ^a   Suga, Seiji ^a   Tanaka, Hideo ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; ARYLBORONIC ACID; BORONIC ACID DERIVATIVE; PALLADIUM; SILVER; SILVER ACETYLIDE; SILVER DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; ELECTROCHEMISTRY; OXIDATION; SONOGASHIRA REACTION; SYNTHESIS;

EID: 78649684434     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/c0cc02633f     Document Type: Article

References (17)

1. U. Halbes-Letinois J.-M. Weibel P. Pale Chem. Soc. Rev. 2007 36 759
2. Recent examples, see: S. Kim B. Kim J. In Synthesis 2009 1963
3. B. J. Albert K. Koide J. Org. Chem. 2008 73 1093
4. R. H. Pouwer J. B. Harper K. Vyakaranam J. Michl C. M. Williams C. H. Jessen P. V. Bernhardt Eur. J. Org. Chem. 2007 241
5. R. H. Pouwer C. M. Williams A. L. Raine J. B. Harper Org. Lett. 2005 7 1323
6. S. P. Shahi K. Koide Angew. Chem., Int. Ed. 2004 43 2525
7. D. Bruyere D. Bouyssi G. Balme Tetrahedron 2004 60 4007
8. K. Mitsudo T. Shiraga D. Kagen D. Shi J. Y. Becker H. Tanaka Tetrahedron 2009 65 8384
9. K. Mitsudo T. Ishii H. Tanaka Electrochemistry 2008 76 859
10. K. Mitsudo T. Imura T. Yamaguchi H. Tanaka Tetrahedron Lett. 2008 49 7287
11. K. Mitsudo T. Shiraga H. Tanaka Tetrahedron Lett. 2008 49 6593
12. K. Mitsudo T. Kaide E. Nakamoto K. Yoshida H. Tanaka J. Am. Chem. Soc. 2007 129 2246
13. Pd or Cu-catalysed coupling of terminal alkynes and arylboronic acids, see: G. Zou J. Zhu J. Tang Tetrahedron Lett. 2003 44 8709
14. F. Yang Y. Wu Eur. J. Org. Chem. 2007 3476
15. C. Pan F. Luo W. Wang Z. Ye J. Cheng Tetrahedron Lett. 2009 50 5044
16. J. Mao J. Guo S. J. Ji J. Mol. Catal. A: Chem. 2008 284 85
17. Another plausible mechanism is that transmetallation with a silver acetylide would be the first step, and following transmetallation with arylboronic acid and reductive elimination would afford the coupling product. The details of the mechanism is currently under investigation.