Preparation of 5-membered rings via radical addition-translocation- cyclization (RATC) processes mediated by diethyl thiophosphites

Advanced Synthesis and Catalysis

Volumn 353, Issue 8, 2011, Pages 1353-1358

  Lamarque, Christophe ^a   Beaufils, Florent ^a   Dénès, Fabrice ^a,b   Schenk, Kurt ^c   Renaud, Philippe ^a  

^a UNIVERSITY OF BERN   (Switzerland)

^b UNIVERSITÉ DE NANTES   (France)

^c EPFL   (Switzerland)

Author keywords

1,5 hydrogen transfer; alkynes; dialkyl phosphites; dialkyl thiophosphites; radical initiators; radical reactions

Indexed keywords

EID: 79957537753     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000852     Document Type: Article

References (46)

1. S. C. Fields, Tetrahedron 1999, 55, 12237.
2. V. M. R. dos Santos, C. L. Donnici, J. B. N. DaCosta, J. M. R. Caixeiro, Quimica Nova 2007, 30, 159.
3. C. Y. Yuan, S. S. Li, C. Z. Li, S. J. Chen, W. S. Huang, G. Q. Wang, C. Pan, Y. X. Zhang, Heteroat. Chem. 1997, 8, 103
4. I. P. Beletskaya, M. M. Kabachnik, Mendeleev Commun. 2008, 18, 113.
5. A. K. Bhattacharya, G. Thyagarajan, Chem. Rev. 1981, 81, 415.
6. E. K. Fields, J. Am. Chem. Soc. 1952, 74, 1528
7. M. I. Kabachnik, T. Y. Medved, Izvest. Akad. Nauk SSSR Ser. Khim. 1952, 540.
8. A. N. Pudovik, I. V. Konovalova, Synthesis 1979, 81.
9. A. N. Pudovik, I. V. Konovalova, Zhur. Obshch. Khim. 1959, 29, 3342
10. D. Semenzin, G. Etemad-Moghadam, D. Albouy, O. Diallo, M. Koenig, J. Org. Chem. 1997, 62, 2414
11. A. R. Stiles, W. E. Vaughan, F. F. Rust, J. Am. Chem. Soc. 1958, 80, 714
12. R. L. Kenney, G. S. Fisher, J. Org. Chem. 1974, 39, 682
13. H. J. Callot, C. Benezra, Can. J. Chem. 1971, 49, 500
14. D. Leca, L. Fensterbank, E. Lacote, M. Malacria, Chem. Soc. Rev. 2005, 34, 858.
15. J. M. Barks, B. C. Gilbert, A. F. Parsons, B. Upeandran, Tetrahedron Lett. 2001, 42, 3137
16. M. P. Healy, A. F. Parsons, J. G. T. Rawlinson, Synlett 2008, 329
17. C. M. Jessop, A. F. Parsons, A. Routledge, D. J. Irvine, Tetrahedron Lett. 2004, 45, 5095.
18. M. P. Healy, A. F. Parsons, J. G. T. Rawlinson, Org. Lett. 2005, 7, 1597.
19. T. A. Hunt, A. F. Parsons, R. Pratt, J. Org. Chem. 2006, 71, 3656.
20. C. M. Jessop, A. F. Parsons, A. Routledge, D. J. Irvine, Eur. J. Org. Chem. 2006, 1547.
21. J. E. Brumwell, N. S. Simpkins, N. K. Terrett, Tetrahedron 1994, 50, 13533
22. J. E. Brumwell, N. S. Simpkins, N. K. Terrett, Tetrahedron Lett. 1993, 34, 1215
23. O. Tayama, A. Nakano, T. Iwahama, S. Sakaguchi, Y. Ishii, J. Org. Chem. 2004, 69, 5494
24. P. Carta, N. Puljic, C. Robert, A.-L. Dhimane, C. Ollivier, L. Fensterbank, E. LacÃte, M. Malacria, Tetrahedron 2008, 64, 11865
25. P. Carta, N. Puljic, C. Robert, A. L. Dhimane, L. Fensterbank, E. LacÃte, M. Malacria, Org. Lett. 2007, 9, 1061.
26. C. M. Jessop, A. F. Parsons, A. Routledge, D. J. Irvine, Tetrahedron: Asymmetry 2003, 14, 2849.
27. F. Dénès, F. Beaufils, P. Renaud, Org. Lett. 2007, 9, 4375
28. M. Lachia, F. Dénès, F. Beaufils, P. Renaud, Org. Lett. 2005, 7, 4103.
29. F. Beaufils, F. Dénès, B. Becattini, P. Renaud, K. Schenk, Adv. Synth. Catal. 2005, 347, 1587.
30. F. Beaufils, F. Dénès, P. Renaud, Org. Lett. 2004, 6, 2563.
31. D. P. Curran, D. Kim, C. Ziegler, Tetrahedron 1991, 47, 6189.
32. D. P. Curran, W. Shen, J. Am. Chem. Soc. 1993, 115, 6051.
33. F. Dénès, F. Beaufils, P. Renaud, Synlett 2008, 2389
34. P. Renaud, F. Beaufils, F. Dénès, L. Feray, C. Imboden, N. Kuznetsov, Chimia 2008, 62, 510.
35. F. G. Bordwell, X.-M. Zhang, A. V. Satish, J. P. Cheng, J. Am. Chem. Soc. 1994, 116, 6605
36. Y.-R. Luo, Handbook of Bond Dissociation Energies in Organic Compounds, CRC Press, Boca Raton, 2003.
37. F. Beaufils, F. Dénès, P. Renaud, Angew. Chem. 2005, 117, 5407
38. Angew. Chem. Int. Ed. 2005, 44, 5273.
39. C. K. Sha, C. W. Hsu, Y. T. Chen, S. Y. Cheng, Tetrahedron Lett. 2000, 41, 9865.
40. S. R. Piettre, Tetrahedron Lett. 1996, 37, 2233
41. T. F. Herpin, W. B. Motherwell, B. P. Roberts, S. Roland, J. M. Weibel, Tetrahedron 1997, 53, 15085
42. A. Gautier, G. Garipova, O. Dubert, H. Oulyadi, S. R. Piettre, Tetrahedron Lett. 2001, 42, 5673.
43. M. V. Encinas, E. A. Lissi, J. Photochem. 1982, 20, 153.
44. I. De Riggi, J. M. Surzur, M. P. Bertrand, A. Archavlis, R. Faure, Tetrahedron 1990, 46, 5285
45. M. E. Kuehne, R. E. Damon, J. Org. Chem. 1977, 42, 1825.
46. CCDC 778530 contains supplementary crystallographic information for 7a. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K.; E-mail: deposit@ccdc.cam.ac.uk.