Zinc-mediated alkynylation of carbonyl compounds with iodoalkynes: a facile synthesis of propargyl alcohols

Tetrahedron Letters

Volumn 49, Issue 50, 2008, Pages 7132-7134

  Srihari, P ^a   Singh, Vinay K ^a   Bhunia, Dinesh C ^a   Yadav, J S ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALKYNE DERIVATIVE; CARBONYL DERIVATIVE; PROPARGYL ALCOHOL; UNCLASSIFIED DRUG; ZINC;

ALKYNYLATION; ARTICLE; CHEMICAL REACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 54449092856     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.09.156     Document Type: Article

References (36)

1. Pu L. Tetrahedron 59 (2003) 9873-9886
2. Stephane G., Aline B., Karen P., Annie L., and Arnaud H. Chem. Rev. 106 (2006) 2355-2403
3. Koyuncu H., and Dogan O. Org. Lett. 9 (2007) 3477-3479
4. Hudrlik P.F., and Hudrlik A.M. The Chemistry of the Carbon-Carbon Triple Bond Part 1. In: Patai S. (Ed) (1978), John Wiley and Sons, New York 256
5. For examples see:. Sierra M.A., and Torres M.R. J. Org. Chem. 72 (2007) 4213-4219
6. Tominaga H., Maezaki N., Yanai M., Kojima N., Urabe D., Ueki R., and Tanaka T. Eur. J. Org. Chem. (2006) 1422-1429
7. Trost B.M., and Weiss A.H. Org. Lett. 8 (2006) 4461-4464
8. Srihari P., Bhunia D.C., Sreedhar P., and Yadav J.S. Synlett (2008) 1045-1049
9. Yadav J.S., Bhunia D.C., Vamshi Krishna K., and Srihari P. Tetrahedron Lett. 48 (2007) 8306-8310
10. Srihari P., Shyam Sunder Reddy J., Bhunia D.C., Mandal S.S., and Yadav J.S. Synth. Commun. 38 (2008) 1448-1455
11. Srihari P., Shyam Sunder Reddy J., Mandal S.S., Satyanaraya K., and Yadav J.S. Synthesis (2008) 1853-1860
12. Imamoto T., Sugiura Y., and Takiyama N. Tetrahedron Lett. 25 (1984) 4233-4236
13. Brown H.C., Molander G.A., Singh S.M., and Racherla U.S. J. Org. Chem. 50 (1985) 1577-1582
14. Hirao T., Misu D., and Agawa T. Tetrahedron Lett. 27 (1986) 933-934
15. Ahn J.H., Joung M.J., Yoon N.M., Oniciu D.C., and Katrizky A.R. J. Org. Chem. 64 (1999) 488-492 and references therein
16. For a few representative examples see:. Yamaguchi M., Hayashi A., and Hirama M. Chem. Lett. (1992) 2479-2482
17. Han Y., and Huang Y.-Z. Tetrahedron Lett. 36 (1995) 7277-7280
18. Frantz D.E., Fassler R., and Carreira E.M. J. Am. Chem. Soc. 121 (1999) 11245-11246
19. Sakai N., Hirasawa M., and Konakahara T. Tetrahedron Lett. 44 (2003) 4171-4174
20. Harada S., Takita R., Oshmia T., Matsunaga S., and Shibasaki M. Chem. Commun. (2007) 948-950
21. For recent representative examples see:. Wang Q., Chen S.-Y., Yu H.-Q., and Pu L. Tetrahedron 63 (2007) 4422-4428
22. Trost B.M., Weiss A.H., and Wangelin A.J. J. Am. Chem. Soc. 128 (2006) 8-9
23. Brezhnev L.Yu., Vartanyan M.M., and Khandin A.V. Chem. Heterocycl. Compd. 27 (1991) 132-134
24. Munetaka K., Shinobu T., Kazuhiro K., Kazuhito H., and Shohei T. Tetrahedron Lett. 36 (1995) 3707-3710
25. Munetaka K., Daisuke N., Shinobu T., Kazuhito H., and Shohei T. Tetrahedron 56 (2000) 9927-9936
26. Jacques A., Nadege L.G., and Latifa S. Tetrahedron Lett. (2002) 5255-5256
27. Natalia M.-V., Julia K., and Ilan M. Synthesis (2000) 917-920
28. Kazuhiko T., Tooru K., Shigeki N., Koichiro O., and Hitosi N. Tetrahedron Lett. 45 (1985) 5585-5588
29. Xuefeng J., Hongwei Y., Ling F., and Chengjian Z. Tetrahedron Lett. 49 (2008) 1370-1372
30. For our earlier contributions with zinc mediated organic transformations see:. Srihari P., Singh A.P., Basak A.K., and Yadav J.S. Tetrahedron Lett. 48 (2007) 5999-6001
31. Yadav J.S., Reddy B.V.S., Kondaji G., Srinivasa Rao R., and Praveen Kumar S. Tetrahedron Lett. 43 (2002) 8133-8135
32. Yadav J.S., Meshram H.M., Sudershan Reddy G., and Muralidhar Reddy M. Synth. Commun. 28 (1998) 2203-2206
33. Yadav J.S., and Barma D.K. Tetrahedron 52 (1996) 4457-4466
34. 4Cl solution. The organic layer was concentrated and the residue was purified by column chromatography (ethyl acetate/hexane) to yield the pure product.
35. 18ONa, 237.1255: found 237.1250.
36. Acetophenone and benzophenone did not respond to the present protocol.