Silylation of 1-alkynes with chlorosilanes promoted by Zn(OTf) 2: An efficient way to the preparation of alkynylsilanes

Tetrahedron Letters

Volumn 46, Issue 3, 2005, Pages 517-519

  Jiang, Huiling ^a   Zhu, Shizheng ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Alkynylsilanes; Terminal alkynes silylation; Zinc triflate

Indexed keywords

ALKYNE DERIVATIVE; ALKYNYL GROUP; SILANE DERIVATIVE; ZINC DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; REACTION ANALYSIS; SILYLATION; STRUCTURE ANALYSIS;

EID: 11144290705     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.10.175     Document Type: Article

References (23)

1. G. Brizius, and U.H.F. Bunz Org. Lett. 4 2002 2829 2832
2. T. Schubert, W. Hummel, and M.-R. Kula Eur. J. Org. Chem. 23 2001 4181 4188
3. H. Jian, and J.M. Tour J. Org. Chem. 68 2003 5091 5103
4. M.J. Plater, and T. Jackson Tetrahedron 39 2003 4687 4692
5. T. Dingemans, D.J. Photinos, and E.T. Samulski J. Chem. Phys. 2003 7046 7061
6. R.S. Loewe, R.K. Lammi, and J.R. Diers J. Mater. Chem. 12 2002 1530 1552
7. D. Kumaresan, N. Agarwal, and I. Gupta Tetrahedron 58 2002 5343 5356
8. L.L. Schafer, J.R. Nitschke, and S.S.H. Mao Chem. Eur. J. 2002 74 83
9. G.W. Kanalka, L. Wang, and R.M. Pagni Tetrahedron 57 2001 8017 8028
10. C. Eaborn J. Am. Chem. Soc. 89 1967 1364 1366
11. W.P. Weber J. Org. Chem. 36 1971 1620 1626
12. J. Kurita, M. Ishii, and S. Yasuike J. Chem. Soc., Chem. Commun. 1993 1309 1310
13. M.E. Freeburger, and L. Spialter J. Org. Chem. 35 1970 652 657
14. H.-U. Siehl, F.-P. Koufman, and L. Hori J. Am. Chem. Soc. 114 1992 9343 9349
15. S. Hikaru, H. Yasuo, and H. Tamejiro Tetrahedron Lett. 36 1995 2769 2772
16. A.A. Aleksey, V.K. Valeri, and V.K. Nikotlai Org. Lett. 6 2004 421 424
17. 2 was chosen in further experiments
18. Tin acetylenes can be conveniently synthesized through Corey-Fuchs reaction A.M. Gilbert, R. Miller, and W.D. Wulff Tetrahedron 55 1999 1607 1630
19. R. Victoria, and R. Yolande Tetrahedron Lett. 35 1994 4777 4780
20. 4Cl (statd. aqueous, 5 mL) was added. The mixture was extracted with EtOAc (3 × 5 mL). After working up as usual, the crude product was purified by chromatography on silica gel (hexane/AcOEt = 60:1)
21. E.F. Ong, F. Royer, and M.C. Erick J. Am. Chem. Soc. 122 2000 1806 1807
22. L. Shaw-Tao, L. Chuan-Chen, and W.L. David Tetrahedron 56 2000 9619 9624
23. T.G.M. Romas, E. Didier, and B. Loubinoux Synth. Lett. 1 1990 547 550