Sunlight oxidation of alkyl aryl tellurides to the corresponding carbonyl compounds: A new carbonyl precursor

Organic Letters

Volumn 11, Issue 21, 2009, Pages 4870-4873

  Ouchi, Akihiko ^a,b   Hyugano, Takeshi ^b   Liu, Chuanxiang ^a  

^a NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

^b UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 70350635796     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901943f     Document Type: Article

References (41)

1. (a) Science of Synthesis; Brückner, R., Ed.; Georg Thieme Verlag: Stuttgart, 2007; Vol.25.
2. (b) Science of Synthesis; Cossy, J., Ed.; Georg Thieme Verlag: Stuttgart, 2005; Vol.26.
3. Science of Synthesis; Kambe, N., Ed.; Georg Thieme Verlag: Stuttgart, 2008; Vol.39.
4. Review: (a) Martens, J.; Praefcke, K. J. Organomet. Chem. 1980, 198, 321.
5. (b) Goldschmidt, Z. In the Chemistry of Organic Selenium and Tellurium Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, UK, 1987; Vol.2, pp 275-337, Chapter 5.
6. (c) Petragnani, N.; Stefani, H. A. Tetrahedron 2005, 61, 1613.
7. (a) Spencer, H. K.; Cava, M. P. J. Org. Chem. 1977, 42, 2937.
8. (b) Browm, D. H.; Cross, R. J.; Millington, D. J. Organomet. Chem. 1977, 125, 219.
9. (c) Barton, D. H. R.; Ozbalik, N.; Sarma, J. C. Tetrahedron Lett. 1988, 29, 6581.
10. (d) Barton, D. H. R.; Ramesh, M. J. Am. Chem. Soc. 1990, 112, 891.
11. (e) Barton, D. H. R.; Dalko, P. I.; Gero, S. D. Tetrahedron Lett. 1991, 32, 4713.
12. (f) Barton, D. H. R.; Camara, J.; Cheng, X.; Gero, S. D.; Jaszberenyi, J. C.; Quiclet-Sire, B. Tetrahedron 1992, 48, 9261.
13. (g) Bell, W.; Cole-Hamilton, D. J.; Culshaw, P. N.; McQueen, A. E. D.; Shenai-Khatkhate, D. V.; Walton, J. C. J. Organomet. Chem. 1992, 430, 43.
14. (h) Engman, L.; Gupta, V. J. Chem. Soc., Chem. Commun. 1995, 2515.
15. (i) Barton, D. H. R.; Gero, S. D.; Holliday, P.; Quiclet-Sire, B. Tetrahedron 1996, 52, 8233.
16. (j) He, W.; Togo, H.; Ogawa, H.; Yokoyama, M. Heteroat. Chem. 1997, 8, 411.
17. (k) Engman, L.; Gupta, V. J. Org. Chem. 1997, 62, 157.
18. (a) Yamago, S.; Hashidume, M.; Yoshida, J. Chem. Lett. 2000, 1234.
19. (b) Pola, J.; Ouchi, A. J. Organomet. Chem. 2001, 629, 93.
20. (c) Pola, J.; Bastl, Z.; Subrt, J.; Ouchi, A. Appl. Organomet. Chem. 2001, 15, 924.
21. (d) Yamago, S.; Iida, K.; Yoshida, J. Tetrahedron Lett. 2001, 42, 5061.
22. (e) Yamago, S.; Hashidume, M.; Yoshida, J. Tetrahedron 2002, 58, 6805, and references cited therein.
23. Mason, W. R. J. Phys. Chem. 1996, 100, 8139.
24. Yamago, S.; Ukai, Y.; Matsumoto, A.; Nakamura, Y. J. Am. Chem. Soc. 2009, 131, 2100.
25. Original data and/or experimental details are given as Supporting Information.
26. Yields of the products are based on the consumed starting material. The results are the average of at least two independent runs.
27. Hyugano, T.; Liu, S.; Ouchi, A. J. Org. Chem. 2008, 73, 8861.
28. Batt, L. In the Chemistry of Organic Selenium and Tellurium Compounds; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, UK, 1986; Vol.1, pp 158-160, Chapter 4.
29. Ouchi, A.; Liu, S.; Li, Z.; Kumar, S. A.; Suzuki, T.; Hyugano, T.; Kitahara, H. J. Org. Chem. 2007, 72, 8700.
30. (a) Esser, P.; Pohlmann, B.; Scharf, H.-D. Angew. Chem., Int. Ed. Engl. 1994, 33, 2009.
31. (b) Funken, K.-H.; Becker, M. Renew. Energy 2001, 24, 469.
32. (c) Schiel, C.; Oelgemoller, M.; Ortner, J.; Mattay, J. Green Chem. 2001, 3, 224.
33. (d) Rüther, T.; Bond, A. M.; Jackson, W. R. Green Chem. 2003, 5, 364.
34. (e) Li, J.-T.; Yang, J.-H.; Han, J.-F.; Li, T.-S. Green Chem. 2003, 5, 433.
35. (f) Doohan, R. A.; Geraghty, N. W. A. Green Chem. 2005, 7, 91.
36. (g) Itoh, A.; Hashimoto, S.; Kuwabara, K.; Kodama, T.; Masaki, Y. Green Chem. 2005, 7, 830.
37. (h) Walspurger, S.; Vasilyev, A. V.; Sommer, J.; Pale, P. Tetrahedron 2005, 61, 3559.
38. (i) Jung, C.; Funken, K.-H.; Ortner, J. Photochem. Photobiol. Sci. 2005, 4, 409.
39. (j) Oelgemöller, M.; Jung, C.; Mattay, J. Pure Appl. Chem. 2007, 79, 1939. and references cited therein.
40. (k) Selvam, K.; Swaminathan, M. Chem. Lett. 2007, 36, 1060.
41. (l) Yan, P.; Wang, R.; Wu, S.; Lei, Z. Catal. Commun. 2008, 9, 406.