Synthesis of siloles via rhodium-catalyzed cyclization of alkynes and diynes with hexamethyldisilane

Synlett

Volumn , Issue 6, 2011, Pages 813-816

  Matsuda, Takanori ^a   Suda, Yuya ^a   Fujisaki, Yosuke ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

alkynes; cyclization; diynes; rhodium; siloles

Indexed keywords

1,6 DIYNE DERIVATIVE; ALKYNE DERIVATIVE; CHEMICAL COMPOUND; HEXAMETHYLDISILANE; RHODIUM; SILOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; PROCESS OPTIMIZATION; PURIFICATION; SILYLATION; SYNTHESIS;

EID: 79953023595     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1259914     Document Type: Article

References (35)

1. Dubac J, Laporterie A, Manuel G, Chem. Rev. 1990 90 215
2. Hissler M, Dyer P W., Réau R, Coord. Chem. Rev. 2003 244 1
3. Yamaguchi S, Tamao K, Chem. Lett. 2005 34 2
4. Yamaguchi S, Tamao K, J. Chem. Soc., Dalton Trans. 1998 3693
5. Chen J, Cao Y, Macromol. Rapid Commun. 2007 28 1714
6. Zhan X, Barlow S, Marder S R., Chem. Commun. 2009 1948
7. Liu J, Lam J W. Y., Tang B Z., J. Inorg. Organomet. Polym. 2009 19 249
8. Matsuda T, Kadowaki S, Goya T, Murakami M, Org. Lett. 2007 9 133
9. Matsuda T, Kadowaki S, Murakami M, Chem. Commun. 2007 2627
10. Matsuda T, Kadowaki S, Yamaguchi Y, Murakami M, Chem. Commun. 2008 2744
11. Matsuda T, Yamaguchi Y, Murakami M, Synlett 2008 561
12. Matsuda T, Yamaguchi Y, Murakami M, Synlett 2010 2743
13. Ohmura T, Masuda K, Suginome M, J. Am. Chem. Soc. 2008 130 1526
14. Shimizu M, Mochida K, Hiyama T, Angew. Chem. Int. Ed. 2008 47 9760
15. Tobisu M, Onoe M, Kita Y, Chatani N, J. Am. Chem. Soc. 2009 131 7506
16. Ureshino T, Yoshida T, Kuninobu Y, Takai K, J. Am. Chem. Soc. 2010 132 14324
17. For earlier studies on catalytic construction of silole skeletons, see:, Okinoshima H, Yamamoto K, Kumada M, J. Am. Chem. Soc. 1972 94 9263
18. Sakurai H, Kamiyama Y, Nakadaira Y, J. Am. Chem. Soc. 1977 99 3879
19. Seyferth D, Vick S C., Shannon M L., Lim T F. O., Duncan D P., J. Organomet. Chem. 1977 135 C37
20. Schäfer A, Weidenbruch M, Pohl S, J. Organomet. Chem. 1985 282 305
21. Ikenaga K, Hiramatsu K, Nasaka N, Matsumoto S, J. Org. Chem. 1993 58 5045
22. Ojima I, Fracchiolla D A., Donovan R J., Banerji P, J. Org. Chem. 1994 59 7594
23. Palmer W S., Woerpel K A., Organometallics 1997 16 1097
24. For reviews, see:, Han L.-B, Tanaka M, Chem. Commun. 1999 395
25. Beletskaya I, Moberg C, Chem. Rev. 2006 106 2320
26. Suginome M, Matsuda T, Ohmura T, Seki A, Murakami M, In Comprehensive Organometallic Chemistry III Vol. 10 Crabtree R Mingos M Ojima I Elsevier Oxford 2007 725
27. Walter C, Auer G, Oestreich M, Angew. Chem. Int. Ed. 2006 45 5675
28. Nakao Y, Chen J, Imanaka H, Hiyama T, Ichikawa Y, Duan W.-L, Shintani R, Hayashi T, J. Am. Chem. Soc. 2007 129 9137
29. Walter C, Fröhlich R, Oestreich M, Tetrahedron 2009 65 5513
30. Tobisu M, Kita Y, Chatani N, J. Am. Chem. Soc. 2006 128 8152
31. Tobisu M, Ano Y, Chatani N, Chem. Asian J. 2008 3 1585
32. Tobisu M, Kita Y, Ano Y, Chatani N, J. Am. Chem. Soc. 2008 130 15982
33. Kita Y, Tobisu M, Chatani N, Org. Lett. 2010 12 1864
34. For Si-Me bond cleavage observed in palladium-catalyzed reactions, see:, Rauf W, Brown J M., Angew. Chem. Int. Ed. 2008 47 4228
35. Nakao Y, Takeda M, Matsumoto T, Hiyama T, Angew. Chem. Int. Ed. 2010 49 4447