Mild and efficient oxy-iodination of alkynes and phenols with potassium iodide and tert-butyl hydroperoxide

Tetrahedron Letters

Volumn 51, Issue 16, 2010, Pages 2170-2173

  Rajender Reddy, K ^a   Venkateshwar, M ^a   Uma Maheswari, C ^a   Santhosh Kumar, P ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Alkynes; Iodination; Peroxide; Phenols; Potassium iodide

Indexed keywords

1 IODOALKYNE DERIVATIVE; ALKYNE DERIVATIVE; IODOPHENOL DERIVATIVE; PHENOL DERIVATIVE; POTASSIUM IODIDE; TERT BUTYL HYDROPEROXIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; IODINATION; REACTION ANALYSIS; SYNTHESIS;

EID: 77949491887     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.02.074     Document Type: Article

References (55)

1. Boutin R.H., and Rapoport H. J. Org. Chem. 51 (1986) 5320-5327
2. Bjorkling F., Norin T., and Unelius R. Synth. Commun. 15 (1985) 463-472
3. Hofmeister H., Annen K., Laurent H., and Wiechert R. Angew. Chem., Int. Ed. Engl. 23 (1984) 727-729
4. Roush W.R., Peseckis S.M., and Walts A.E. J. Org. Chem. 49 (1984) 3429-3432
5. Jeffery T. J. Chem. Soc., Chem. Commun. (1988) 909-910 and references cited therein
6. Kabalka G.W., Shoup T.M., Daniel G.B., and Goodman M.M. Nucl. Med. Biol. 27 (2000) 279-287
7. Abe H., and Suzuki H. Bull. Chem. Soc. Jpn. 72 (1999) 787-798
8. Nishikawa T., Shibaya S., Hosokowa S., and Isobe M. Synlett (1994) 485-486
9. Casarini A., Dembech P., Reginato G., Ricci A., and Seconi G. Tetrahedron Lett. 32 (1991) 2169-2170
10. Ricci A., Taddei M., Dembech P., Guerrini A., and Seconi G. Synthesis (1989) 461-463
11. Heasley V.L., Shellhamer D.F., Heasley L.E., and Yaeger B.D. J. Org. Chem. 45 (1980) 4649-4652
12. Kabalka G.W., and Mereddy A.R. Tetrahedron Lett. 45 (2004) 1417-1419
13. Nishiguchi I., Kanbe O., Itoh K., and Maekawa H. Synlett (2000) 89-91
14. Yan J., Li J., and Cheng D. Synlett (2007) 2442-2444
15. Stang P.J., and Surber B.W. J. Am. Chem. Soc. 107 (1985) 1452-1453
16. Barluenga J., Gonzalez J.M., Rodriguez M.A., Compos P.G., and Asensio G. Synthesis (1987) 661-662
17. Ochiai M., and Uemura K. J. Am. Chem. Soc. 115 (1993) 2528-2529
18. Brunel Y., and Rousseau G. Tetrahedron Lett. 36 (1995) 2619-2622
19. Meng L.G., Cai P.J., Guo Q.X., and Xue S. Synth. Commun. 38 (2008) 225-231
20. Russo M.V., Sterzo C.L., Franceschini P., Biagini G., and Furlani A. J. Organomet. Chem. 619 (2001) 49-61
21. Nasker D., and Roy S. J. Org. Chem. 64 (1999) 6896-6897
22. Stefani H.A., Cella R., Dorr F.A., Pereira M.P.D., Gomes F.P., and Zeni G. Tetrahedron Lett. 46 (2005) 2001-2003
23. Cohen M.J., and McNelis E. J. Org. Chem. 49 (1984) 515-518
24. Rao M.L.N., and Periasamy M. Synth. Commun. 25 (1995) 2295-2299
25. Luithle J.E.A., and Pietruszka J. Eur. J. Org. Chem. (2000) 2557-2562
26. Lee G.C.M., Tobias B., Holmes J.M., Harcourt D.A., and Garst M.E. J. Am. Chem. Soc. 112 (1990) 9330-9336
27. Blackmore I.J., Boa A.N., Murray E.J., Dennis M., and Woodward S. Tetrahedron Lett. 40 (1999) 6671-6672
28. Seevers R.H., and Counsell R.E. Chem. Rev. (1982) 575-590
29. Merkushev E.B. Synthesis (1988) 923-937
30. Diederich F., and Stang P.J. Metal-catalyzed Cross-coupling Reactions (1997), Wiley-VCH, New York
31. Virgil S.C. In: Paquette L.A. (Ed). Encyclopedia of Reagents for Organic Synthesis Vol. 4 (1995), Wiley, Chichester
32. Barluenga J. Pure Appl. Chem. 71 (1999) 431 and references therein
33. Hanson J.R. J. Chem. Res. (2006) 277
34. Johnsson R., Meijer A., and Ellervik U. Tetrahedron 61 (2005) 11657
35. Narender N., Srinivasu P., Kulkarani S.J., and Raghavan K.V. Synth. Commun. 32 (2002) 2319-2324
36. Adimurthy S., Ramachandraiah G., Gosh K.P., and Bedekar V.A. Tetrahedron Lett. 44 (2003) 5099-5101
37. Iskra J., Stavber S., and Zupan M. Synthesis (2004) 1869-1873
38. Sathiyapriya R., and Karunakaran J.R. Synth. Commun. 36 (2006) 1915-1917
39. Emmanuvel L., Shukla K.R., Sudalai A., Gurunath S., and Sivaram S. Tetrahedron Lett. 47 (2006) 4793-4796
40. Reza A.P., and Mersieh G. Chin. J. Chem. 24 (2006) 1077-1079
41. Togo H., and Iida S. Synlett (2006) 2159-2175 and references therein
42. Podgorsek A., Zupan M., and Iskra J. Angew. Chem., Int. Ed. Engl. 48 (2009) 8424-8450
43. Stavber S., Jereb M., and Zupan M. Synthesis (2008) 1487-1513 and references cited therein
44. Reddy K.R., Maheswari C.U., Venkateshwar M., and Kantam M.L. Eur. J. Org. Chem. (2008) 3619-3622
45. Reddy K.R., Maheswari C.U., Venkateshwar M., and Kantam M.L. Adv. Synth. Catal. 351 (2009) 93-96
46. Reddy K.R., Maheswari C.U., Venkateshwar M., Prashanthi S., and Kantam M.L. Tetrahedron Lett. 50 (2009) 2050-2054
47. Reddy K.R., Venkateshwar M., Maheswari C.U., and Prashanthi S. Synth. Commun. 40 (2010) 186-195
48. 1H NMR spectroscopy, gas chromatography, and GC-MS.
49. 1H NMR spectroscopy, gas chromatography, and GC-MS.
50. Wu M.Y., Deng J., Li Y., and Chen Y.Q. Synthesis (2005) 1314-1318
51. Kuijpers B.H.M., Dijkmans G.C.T., Groothuys S., Quaedflieg P.J.L.M., Blaauw R.H., Delft F.L.V., and Rutjes F.P.J.T. Synlett (2005) 3059-3062
52. Wu M.Y., Deng J., and Chen Y.Q. Synlett (2006) 645-647
53. Li L., Zhang G., Zhu A., and Zhang L. J. Org. Chem. 73 (2008) 3630-3633
54. Hein E.J., Tripp C.J., Krasnova B.L., Sharpless B.K., and Fokin V.V. Angew. Chem., Int. Ed. Engl. 48 (2009) 8018-8021
55. Smith W.N., Polenz P.b., Johnson B.S., and Dzyuba V.S. Tetrahedron Lett. 51 (2010) 550-553