Thiophenol-mediated 1,5-hydrogen atom abstraction: Easy access to mono- and bicyclic compounds

Advanced Synthesis and Catalysis

Volumn 347, Issue 11-13, 2005, Pages 1587-1594

  Beaufils, Florent ^a   Dénès, Fabrice ^a   Becattini, Barbara ^a   Renaud, Philippe ^a   Schenk, Kurt ^b  

^a UNIVERSITY OF BERN   (Switzerland)

^b EPFL   (Switzerland)

Author keywords

Alkynes; Cyclization; Hydrogen transfer; Radicals; Spiro compounds; Sulfur

Indexed keywords

EID: 27544469847     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200505211     Document Type: Article

References (61)

1. For general reviews on radical reactions, see: B. Giese, in: Radicals in Organics Synthesis: Formation of Carbon-Carbon Bonds, Pergamon: Oxford, 1988;
2. D. P. Curran, in: Comprehensive Organic Synthesis, (Eds.: B. M. Trost, I. Fleming, M. F. Semmelhack), Pergamon: Oxford, 1991, Vol. 4, pp 715 and 779;
3. W. B. Motherwell, D. Crich, in: Free Radical Chain Reactions in Organic Synthesis; Academic Press: London, 1992;
4. J. Fossey, D. Lefort, J. Sorba, in: Free Radicals in Organic Synthesis, Wiley: Chichester, 1995;
5. Radicals in Organic Synthesis, (Eds.: P. Renaud, M. P. Sibi), Wiley-VCH: Weinheim, 2001;
6. S. Zard, in: Radical Reactions in Organic Synthesis, Oxford University Press: Oxford, 2003.
7. For general reviews on radical hydrogen transfer, see: L. Feray, N. Kuznetzov, P. Renaud, in: Radicals in Organic Synthesis, (Eds.: P. Renaud, M. P. Sibi), Wiley-VCH: Weinheim, 2001, Vol. 2, p 246;
8. J. Robertson, J. Pillai, R. K. Lush, Chem. Soc. Rev. 2001, 30, 94.
9. D. P. Curran, K. Dooseop, L. Hong Tao, S. Wang, J. Am. Chem. Soc. 1988, 110, 5900.
10. D. P. Curran, D. Kim, C. Ziegler, Tetrahedron 1991, 47, 6189.
11. D. P. Curran, W. Shen, J. Am. Chem. Soc. 1993, 115, 6051.
12. M. Yokota, M. Toyota, M. Ihara, Chem. Commun. 2003, 3, 422.
13. M. Sannigrahi, D. L. Mayhew, D. L. J. Clive, J. Org. Chem. 1999, 64, 2776.
14. D. L. J. Clive, W. Yang, A. C. MacDonald, Z. Wang, M. Cantin, J. Org. Chem. 2001, 66, 1966.
15. U. Wille, L. Lietzau, Tetrahedron 1999, 55, 10119.
16. A. Stademann, U. Wille, Aust. J. Chem. 2004, 57, 1055.
17. U. Wille, O. Krüger, A. Kirsch, U. Lüning, Eur. J. Org. Chem. 1999, 3185.
18. E. I. Heiba, R. M. Dessau, J. Am. Chem. Soc. 1967, 89, 3772.
19. S. Bogen, L. Fensterbank, M. Malacria, J. Org. Chem. 1999, 64, 819.
20. A. Martinez-Grau, D. P. Curran, Tetrahedron Lett. 1997, 38, 5679.
21. E. Bosch, M. D. Bachi, J. Org. Chem. 1993, 58, 5581.
22. B. Alcaide, I. M. Rodriguez-Campos, J. Rodriguez-Lopez, A. Rodriguez-Vicente, J. Org. Chem. 1999, 64, 5377.
23. F. Beaufils, F. Dénès, P. Renaud, Angew. Chem. Int. Ed. 2005, 44, 5273.
24. D. Crich, in: Organosulfur Chemistry, Synthetic Aspects, (Ed.: P. Page), Academic Press, San Diego, 1995, p. 49.
25. M. P. Bertrand, C. Ferreri, in: Radicals in Organic Synthesis, Vol. 2, (Eds.: P. Renaud, M. P. Sibi), Wiley-VCH, Weinheim, 2001, p. 485.
26. O. Miyata, Y. Ozawa, I. Ninomiya, T. Naito, Tetrahedron 2000, 56, 6199.
27. O. Miyata, T. Naito, C. R. Acad. Sci. Paris Chimie 2001, 401.
28. O. Miyata, K. Muroya, T. Kobayashi, R. Yamanaka, S. Kajisa, J. Koide, T. Naito, Tetrahedron 2002, 58, 4459.
29. S. D. Burke, K. W. Jung, Tetrahedron Lett. 1994, 35, 5837;
30. for an early investigation, see: J. Griffiths, J. A. Murphy, Tetrahedron 1992, 48, 5543.
31. F. Beaufils, F. Dénès, P. Renaud, Org. Lett. 2004, 6, 2563.
32. P. Renaud, F. Beaufils, L. Feray, K. Schenk, Angew. Chem. Int. Ed. 2003, 42, 4230.
33. Traces of thiophenol are presumably generated from the phenylthiyl radical via hydrogen atom abstraction.
34. -1 (25°C) has been reported: J. A. Franz, B. A. Bushaw, M. S. Alnajjar, J. Am. Chem. Soc. 1989, 111, 268.
35. -1 (80°C) has been measured: C. Chatgilialoglu, M. Newcomb, Adv. Organomet. Chem. 1999, 44, 67.
36. 3SnH, to the best of our knowledge, no rate constant has been determined for the reduction of aryl radicals by thiophenol: S. J. Garden, D. V. Avila, A. L. J. Beckwith, V. W. Bowry, K. U. Ingold, J. Lusztyk J. Org. Chem. 1996, 61, 805.
37. I. De Riggi, J. M. Surzur, M. P. Bertrand, A. Archavlis, R. Faure, Tetrahedron 1990, 46, 5285.
38. M. E. Kuehne, R. E. Damon, J. Org. Chem. 1977, 42, 1825.
39. Montevecchi has investigated the mechanistic aspect of the addition of the phenylthiyl radical to terminal alkynes: L. Benati, P. C. Montevecchi, P. Spagnolo J. Chem. Soc. Perkin Trans. 1, 1992, 1659;
40. L. Capella, P. C. Montevecchi, M. Navacchia J. Org. Chem. 1996, 61, 6783.
41. CCDC 271672 contains the supplementary crystallographic data for this paper. Theses data can be obtained free of charge via www.ccdc.cam.ac.uk//conts/ retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, UK; fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk).
42. M. E. Jung, Synlett 1999, 843.
43. A. L. J. Beckwith, G. Phillipou, A. K. Serelis, Tetrahedron Lett. 1981, 22, 2811.
44. S. Wolff, W. C. Agosta, J. Chem. Res. Synopsis 1981, 78.
45. T. V. Rajanbabu, Acc. Chem. Res. 1991, 24, 139.
46. T. V. Rajanbabu, T. Fukunaga, J. Am. Chem. Soc. 1989, 111, 296.
47. G. Mandville, F. Leyendecker, J.-M. Conia, Bull. Soc. Chim. Fr. 1973, 963.
48. M.-A. Boaventura, J. Drouin, J.-M. Conia, Synthesis 1983, 801.
49. H. Huang, C. J. Forsyth, J. Org. Chem. 1995, 60, 2773.
50. Y. Hashizume, S. Maki, M. Ohashi, H. Niwa, Synth. Commun. 1999, 29, 1223.
51. C. K. Sha, F. C. Lee, H. H. Lin, Chem. Commun. 2001, 39.
52. D. L. J. Clive, M. Cantin, A. Khodabocus, X. Kong, Y. Tao, Tetrahedron 1993, 36, 7917.
53. C. K. Sha, W. Y. Ho, Chem. Commun. 1998, 2709.
54. C. K. Sha, C. W. Hsu, Y. T. Cheng, S. Y. Cheng, Tetrahedron Lett. 2000, 41, 9856.
55. D. C. Lathbury, P. J. Parson, I. Pinto, J. Chem. Soc. Chem. Commun. 1988, 81.
56. A. D. Borthwick, S. Caddick, P. J. Parsons, Tetrahedron Lett. 1990, 31, 6914.
57. A. D. Borthwick, S. Caddick, P. J. Parsons, Tetrahedron 1992, 48, 10655.
58. The relative configuration of the major diastereomer has not been determined.
59. A concise synthesis of (-)-erythrodiene has been recently achieved in our laboratory: M. Lachia, F. Dénès, F. Beaufils, P. Renaud, Org. Lett. 2005, 7, 4103.
60. Y. Hiroshi, H. Masaaki, S. Takao, S. Takayuki, S. Mataichi, M. Michinao, Heterocycles 1983, 8, 1541.
61. C. F. Thompson, T. F. Jamison, E. N. Jacobsen, J. Am. Chem. Soc. 2001, 123, 9974.