Sodium nitrite (NaNO2) catalysed iodo-cyclisation of alkenes and alkynes using molecular oxygen

Tetrahedron Letters

Volumn 49, Issue 28, 2008, Pages 4424-4426

  Liu, Hongjun ^a   Pan, Yuanhang ^a   Tan, Choon Hong ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; ACETYL HYPOIODITE; ALKENE DERIVATIVE; ALKYNE DERIVATIVE; ALLYL COMPOUND; CARBAMIC ACID DERIVATIVE; IODINE DERIVATIVE; OXYGEN; SODIUM NITRITE; TETRA N BUTYLAMMONIUM IODIDE;

AMINATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CYCLIZATION; IODINATION;

EID: 44649156311     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.05.013     Document Type: Article

References (37)

1. For reviews, see:. Ishii Y., Sakaguchi S., and Iwahama T. Adv. Synth. Catal. 343 (2001) 393-427
2. Monnier J.R. Appl. Catal., A 221 (2001) 73-91
3. Stratakis M., and Orfanopoulos M. Tetrahedron 56 (2000) 1595-1615
4. Liu R., Liang X., Dong C., and Hu X. J. Am. Chem. Soc. 126 (2004) 4112-4113
5. Liu R., Dong C., Liang X., Wang X., and Hu X. J. Org. Chem. 70 (2005) 729-731
6. Herreri{dotless}́as C.I., Zhang T.Y., and Li C.-J. Tetrahedron Lett. 47 (2006) 13-17
7. Mu R., Liu Z., Yang Z., Liu Z., Wu L., and Liu Z.-L. Adv. Synth. Catal. 347 (2005) 1333-1336
8. Wang N., Liu R., Chen J., and Liang X. Chem. Commun. (2005) 5322-5324
9. Iskra J., Stavber S., and Zupan M. Tetrahedron Lett. 49 (2008) 893-895
10. Liang X., Fu D., Liu R., Zhang Q., Zhang T.Y., and Hu X. Angew. Chem., Int. Ed. 44 (2005) 5520-5523
11. Dowle M.D., and Davies D.I. Chem. Soc. Rev. 8 (1979) 171-197
12. Roux M.-C., Paugam R., and Rousseau G. J. Org. Chem. 66 (2001) 4304-4310
13. Chavan S.P., and Sharma A.K. Tetrahedron Lett. 42 (2001) 4923-4924
14. Mellegaard S.R., and Tunge J.A. J. Org. Chem. 69 (2004) 8979-8981
15. Blot V., Reboul V., and Metzner P. J. Org. Chem. 69 (2004) 1196-1201
16. Royer A.C., Mebane R.C., and Swafford A.M. Synlett (1993) 899-900
17. Curini M., Epifano F., Marcotullio M.C., and Montanari F. Synlett (2004) 368-370
18. van Tamelen E.E., and Shamma M. J. Am. Chem. Soc. 76 (1954) 2315-2317
19. Liu H., and Tan C.-H. Tetrahedron Lett. 48 (2007) 8220-8222
20. Krafft G.A., and Katzenellenbogen J.A. J. Am. Chem. Soc. 103 (1981) 5459-5466
21. Spencer R.W., Tam T.F., Thomas E., Robinson V.J., and Krantz A. J. Am. Chem. Soc. 108 (1986) 5589-5597
22. Wu Z., Minhas G.S., Wen D., Jiang H., Chen K., Zimniak P., and Zheng J. J. Med. Chem. 47 (2004) 3282-3294
23. Biloski A.J., Wood R.D., and Ganem B. J. Am. Chem. Soc. 104 (1982) 3233-3235
24. Hirama M., Iwashita M., Yamazaki Y., and Ito S. Tetrahedron Lett. 25 (1984) 4963-4964
25. Knapp S., and Levorse A.T. J. Org. Chem. 53 (1988) 4006-4014
26. Fujita M., Kitagawa O., Suzuki T., and Taguchi T. J. Org. Chem. 62 (1997) 7330-7335
27. Kitagawa O., Fujita M., Li H., and Taguchi T. Tetrahedron Lett. 38 (1997) 615-618
28. Lei A., Lu X., and Liu G. Tetrahedron Lett. 45 (2004) 1785-1788
29. 2 and AgOAc, see:. Barnett J.R., Andrews L.J., and Keefer R.M. J. Am. Chem. Soc. 94 (1972) 6129-6134
30. Beebe T.R., Barnes B.A., Bender K.A., Halbert A.D., Miller R.D., Ramsay M.T., and Ridenour M.W. J. Org. Chem. 40 (1975) 1992-1994
31. Cambie R.C., Chambers D., Rutledge P.S., and Woodgate P.D. J. Chem. Soc., Perkin Trans. 1 (1978) 1483-1485
32. Rubottome G.M., and Mott R.C. J. Org. Chem. 44 (1979) 1731-1734
33. 2 and PIDA, see:. Courtneidge J.L., Lusztyk J., and Pagé D. Tetrahedron Lett. 35 (1994) 1003-1006
34. Giri R., Chen X., and Yu J.-Q. Angew. Chem., Int. Ed. 44 (2005) 2112-2115
35. Giri R., Chen X., Hao X.-S., Li J.-J., Fan Z.-P., and Yu J.-Q. Tetrahedron: Asymmetry 16 (2005) 3502-3505
36. Wang D.-H., Hao X.-S., Wu D.-F., and Yu J.-Q. Org. Lett. 8 (2006) 3387-3390
37. Giri R., Wasa M., Breazzano S.P., and Yu J.-Q. Org. Lett. 8 (2006) 5685-5688