Straightforward and highly efficient catalyst-free regioselective reaction of thiol to β-nitrostyrene: a concise synthesis of vinyl sulfide and nitro sulfide

Tetrahedron

Volumn 65, Issue 19, 2009, Pages 3878-3885

  Chu, Cheng Ming ^a   Tu, Zhijay ^a   Wu, Pohsi ^a   Wang, Chieh Chieh ^a   Liu, Ju Tsung ^a   Kuo, Chun Wei ^a   Shin, Yu Hsuan ^a   Yao, Ching Fa ^a  

^a NATIONAL TAIWAN NORMAL UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

NITRO SULFIDE; NITROSTYRENE; SOLVENT; STYRENE DERIVATIVE; SULFIDE; THIOL; UNCLASSIFIED DRUG; VINYL SULFIDE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; SUBSTITUTION REACTION; SYNTHESIS; THERMODYNAMICS;

EID: 63549105641     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.02.074     Document Type: Article

References (68)

1. Corey E.J., and Estreicher H. J. Am. Chem. Soc. 100 (1978) 6294-6295
2. Seebach D., Colvin E.W., and Weller T. Chimia 33 (1979) 1-18
3. Barrett A.G.M., and Graboski G.G. Chem. Rev. 86 (1986) 751-762
4. Rosini G., and Ballini R. Synthesis (1988) 833-847
5. Kabalka G.W., Guindi L.H.M., and Varma R.S. Tetrahedron 46 (1990) 7443-7457
6. Lewis R.J., and Moodie R.B. J. Chem. Soc., Perkin Trans. 2 (1997) 563-568
7. Adams J.P., and Paterson J.R. J. Chem. Soc., Perkin Trans. 1 (1999) 749-764
8. Adams J.P., and Paterson J.R. J. Chem. Soc., Perkin Trans. 1 (2000) 3695-3705
9. Perekalin V.V., Lipina E.S., Berestovitskaya V.M., and Efremov D.A. Nitroalkenes, Conjugated Nitro Compounds (1994), Wiley & Sons, Chichester, UK
10. Olah G.A., Malhotra R., and Narang S.C. Nitration: Methods and Mechanisms (1989), VCH, New York, NY
11. Ono N. The Nitro Group in Organic Synthesis (2001), Wiley-VCH, New York, NY
12. Yao C.-F., Chu C.-M., and Liu J.-T. J. Org. Chem. 63 (1998) 719-722
13. Chu C.-M., Liu J.-T., Lin W.-W., and Yao C.-F. J. Chem. Soc., Perkin Trans. 1 (1999) 47-52
14. Liu J.-T., Jang Y.-J., Shih Y.-K., Hu S.-R., Chu C.-M., and Yao C.-F. J. Org. Chem. 66 (2001) 6021-6028
15. Seebach D., Schafer H., Schmidt B., and Schreiber M. Angew. Chem., Int. Ed. Engl. 31 (1992) 1587-1588
16. Namboothiri I.N.N., and Hassner A. J. Organomet. Chem. 518 (1996) 69-77
17. Russell G.A., and Yao C.-F. Heteroat. Chem. 3 (1992) 209-218
18. Han Y., Huang Y.-Z., and Zhou C.-M. Tetrahedron Lett. 37 (1996) 3347-3350
19. Trost B.M., and Lavoie A.C. J. Am. Chem. Soc. 105 (1983) 5075-5090
20. Miller R.D., and Hassig R. Tetrahedron Lett. 26 (1985) 2395-2398
21. Cookson R.C., and Persons P.J. J. Chem. Soc., Chem. Commun. (1976) 990a
22. Takeda T., and Fujiwara T. Chem. Lett. 11 (1982) 1113-1116
23. Morris T.H., Smith E.H., and Walsh R. J. Chem. Soc., Chem. Commun. (1987) 964-965
24. Magnus P., and Quagliato D. J. Org. Chem. 50 (1985) 1621-1626
25. Mizuno H., Domon K., Masuya K., Tanino K., and Kuwajima I. J. Org. Chem. 64 (1999) 2648-2656
26. Domon K.M.K., Tanino K., and Kuwajima I. Synlett (1996) 157-158
27. Ichinose Y., Wakamatsu K., Nozaki K., Birbaum J.L., Oshima K., and Utimoto K. Chem. Lett. (1987) 1647-1650
28. Benati L., Montevecchi P.C., and Spagnolo P. J. Chem. Soc., Perkin Trans. 1 (1991) 2103-2109
29. Benati L., Capella L., Montevecchi P.C., and Spagnolo P. J. Chem. Soc., Perkin Trans. 1 (1995) 1035-1038
30. Beauchemin A., and Gareau Y. Phosphorus, Sulfur Silicon Relat. Elem. 139 (1998) 187-192
31. Mcdonald J.W., Corbin J.L., and Newton W.E. Inorg. Chem. 15 (1976) 2056-2061
32. Kuniyasu H., Ogawa A., Sato K.I., Ryu I., Kambe N., and Sonoda N. J. Am. Chem. Soc. 114 (1992) 5902-5903
33. Backvall J.E., and Ericsson A. J. Org. Chem. 59 (1994) 5850-5851
34. Koelle U., Rietmann C., Tjoe J., Wagner T., and Englert U. Organometallics 14 (1995) 703-713
35. Ogawa A., Ikeda T., Kimura K., and Hirao T. J. Am. Chem. Soc. 121 (1999) 5108-5114
36. Sugoh K., Kuniyasu H., Sugae T., Ohtaka A., Takai Y., Tanaka A., Machino C., Kambe N., and Kurosawa H. J. Am. Chem. Soc. 123 (2001) 5108-5109
37. Murahashi S., Yamamura M., Yanagisawa K., Mita N., and Kondo K. J. Org. Chem. 44 (1979) 2408-2417
38. Foa M., Santi R., and Garavaglia F. J. Organomet. Chem. 206 (1981) C29-C32
39. Baranano D., Mann G., and Hartwig J.F. Curr. Org. Chem. 1 (1997) 287-305
40. Rane A.M., Miranda E.I., and Soderquist J.A. Tetrahedron Lett. 35 (1994) 3225-3226
41. Li G.Y. J. Org. Chem. 67 (2002) 3643-3650
42. Bates C.G., Saejueng P., Doherty M.Q., and Venkataraman D. Org. Lett. 6 (2004) 5005-5008
43. Commercon A., Normant J., and Villieras J. J. Organomet. Chem. 93 (1975) 415-421
44. Yatsumonji Y., Okada O., Tsubouchi A., and Takeda T. Tetrahedron 62 (2006) 9981-9987
45. Aucagne V., Tatibouet A., and Rollin P. Tetrahedron 60 (2004) 1817-1826
46. Stephan E., Olaru A., and Jaouen G. Tetrahedron Lett. 40 (1999) 8571-8574
47. Ishida M., Iwata T., Yokoi M., Kaga K., and Kato S. Synthesis (1985) 632-634
48. Kumamoto T., Hosoi K., and Mukaiyam T. Bull. Chem. Soc. Jpn. 41 (1968) 2742-2745
49. Synthesis of nitro sulfide by the conjugate addition of aromatic thiol to β-nitrostyrenes in neat under catalyst and heating conditions was reported. However, in most cases, these are preparing in the presence of expensive or toxic catalyst and the scope of substrate is also not well-investigated:
50. Mustafa A., Hamid A., Harhash E., and Kamel M. J. Am. Chem. Soc. 77 (1955) 3860-3862
51. Cason L.F., and Wanser C.C. J. Am. Chem. Soc. 73 (1951) 142-145
52. Ménand M., and Dalla V. Synlett (2005) 95-98
53. a value in the range of 7-11 and are very good radical carriers during the course of radical reactions. Due to the softness character of thiyl radicals a large number of versatile synthesis involving thiol radicals were developed. In addition, the interception of radical process by reaction at benzylic positions under thermolysis is well-known:. Renaud P., and Sibi M.P. Radicals in Organic Synthesis Vols. 1 and 2 (2001), Wiley-VCH Verlag GmbH, D69469 Weinheim, Federal Republic of Germany
54. a of 10-11 for alkyl thiol has also been reported:. March J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. 4th ed. (1992), Wiley & Sons, New York, NY Chapter 8
55. Andrey O., Alexakis A., and Bernardinelli G. Org. Lett. 5 (2003) 2559-2561
56. Armarego W.L.F. J. Chem. Soc. C (1969) 986-990
57. Bordwell F.G., and Garbisch Jr. E.W. J. Org. Chem. 27 (1962) 3049-3055
58. Kotrusz P., and Toma S. Molecules 11 (2006) 197-205
59. Somanathan R., Rivero I.A., Aguirre G., Ramirez M., Hellberg L.H., and Bakir F. Synth. Commun. 26 (1996) 1023-1030
60. Taniguchi N. J. Org. Chem. 72 (2007) 1241-1245
61. Annunziata A., Galli C., Gentili P., Guarnieri A., Beit-Yannai M., and Rappoport Z. Eur. J. Org. Chem. 13 (2002) 2136-2143
62. Zheng Y., Du X., and Bao W. Tetrahedron Lett. 47 (2006) 1217-1220
63. Manarin F., Roehrs J.A., Prigol M., Alves D., Nogueira C.W., and Zeni G. Tetrahedron Lett. 48 (2007) 4805-4808
64. Ranu B.C., Chattopadhyay K., and Banerjee S. J. Org. Chem. 71 (2006) 423-425
65. Behzadi A., and Owen L.N. J. Chem. Soc., Perkin Trans. 1 (1973) 2733-2737
66. Cao C., Fraser L.R., and Love J.A. J. Am. Chem. Soc. 127 (2005) 17614-17615
67. Silveira C.C., Perin G., Braga A.L., Dabdoub M.J., and Jacob R.G. Tetrahedron 55 (1999) 7421-7432
68. Carpita A., Rossi R., and Scamuzzi B. Tetrahedron Lett. 30 (1989) 2699-2702