Catalytic carbon-sulfur bond formation by amphoteric vanadyl triflate: exploring with thia-Michael addition, thioacetalization, and transthioacetalization reactions

Tetrahedron

Volumn 65, Issue 50, 2009, Pages 10470-10476

  Chen, Chien Tien ^a   Lin, Yow Dzer ^a   Liu, Cheng Yuan ^a  

^a NATIONAL TAIWAN NORMAL UNIVERSITY   (Taiwan)

Author keywords

C S bond formation; Michael addition; Thioacetalization; Vanadyl triflate

Indexed keywords

ACETAL DERIVATIVE; ALDEHYDE; CARBON; KETONE; SULFUR; TRIFLUOROMETHANESULFONIC ACID; VANADYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; MICHAEL ADDITION; PRIORITY JOURNAL; TEMPERATURE MEASUREMENT;

THIA;

EID: 70350734263     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.10.012     Document Type: Article

References (102)

1. Kondo T., and Mitsudo T.-A. Chem. Rev. 100 (2000) 3205
2. Gilchrist T.L. Heterocyclic Chemistry. 3rd ed. (1997), Addison Wesley Longman, Essex
3. Okazaki R. In: Page P. (Ed). Organosulfur Chemistry Vol. 1 (1995), Academic, London 225-258
4. Czarnik A.W. Acc. Chem. Res. 29 (1996) 112
5. Nguyen-Ba N., Brown W.L., Chan L., Lee N., Brasili L., Lafleur D., and Zacharie B. Chem. Commun. (1999) 1245
6. Ashizawa T., Kawashima K., Kanda Y., Gomi K., Okabe M., Ueda K., and Tamaoki T. Anticancer Drugs 10 (1999) 829
7. Dewick P.M. Medicinal Natural Products. 2nd ed. (2002), John Wiley & Sons, West Sussex, England
8. Vardanyan R.S., and Hruby V.J. Synthesis of Essential Drugs (2006), Elsevier, Amsterdam
9. Perlmutter P. Conjugate Addition Reactions in Organic Synthesis (1992), Pergamon, Oxford
10. For recent reviews, see:
11. Sibi M.P., and Manyem S. Tetrahedron 56 (2000) 8033
12. Krause N., and Hoffmann-Röder A. Synthesis (2001) 171
13. Kanemasa S., and Ito K. Eur. J. Org. Chem. (2004) 4741
14. Enders D., Lüttgen K., and Narine A.A. Synthesis (2007) 959
15. Greene T.W., and Wuts P.G.M. Protective Groups in Organic Synthesis. 3rd ed. (1999), John Wiley & Sons, New York, NY
16. For reviews, see:
17. Seebach D. Angew. Chem., Int. Ed. Engl. 8 (1969) 639
18. Grobel B.-T., and Seebach D. Synthesis (1977) 357
19. Seebach D. Angew. Chem., Int. Ed. Engl. 18 (1979) 239
20. Page P.C.B., van Niel M.B., and Prodger J.C. Tetrahedron 45 (1989) 7643
21. Luh T.-Y., and Lee C.-F. Eur. J. Org. Chem. (2005) 3875 and references cited therein
22. Hauptmann H., and Walter W.F. Chem. Rev. 62 (1962) 347
23. In: Chapleur Y. (Ed). Carbohydrate Mimics: Concepts and Methods (1998), Wiley-VCH, Weinheim, Germany Chapter 6
24. Breit B. Angew. Chem., Int. Ed. 37 (1998) 453 and references cited therein
25. For recent reviews, see:
26. Smith III A.B., Condon S.M., and Mccauley J.A. Acc. Chem. Res. 31 (1998) 35
27. Yus M., Najera C., and Foubelo F. Tetrahedron 59 (2003) 6147
28. Smith III A.B., and Adams C.M. Acc. Chem. Res. 37 (2004) 365
29. For recent examples, see:
30. Kamble V.T., Bandgar B.P., Muley D.B., and Joshi N.S. J. Mol. Catal. A: Chem. 268 (2007) 70
31. Shinde P.D., Borate H.B., and Wakharkar R.D. ARKIVOC xiv (2004) 110
32. Firouzabadi H., Eslami S., and Karimi B. Bull. Chem. Soc. Jpn. 74 (2001) 2401
33. Jnaneshwara G.K., Barhate N.B., Sudalai S., Deshpande V.H., Wakharkar R.D., Gajare A.S., Shingare M.S., and Sukumar R. J. Chem. Soc., Perkin Trans. 1 (1998) 965
34. Diez E., Lopez A.M., Pareja C., Martin E., Fernandez R., and Lassaletta M.J. Tetrahedron Lett. 39 (1998) 7955
35. Konosu T., and Oida S. Chem. Pharm. Bull. 39 (1991) 2212
36. Nicolaou K.C., Veale C.A., Hwang C.-K., Hutchinson J., Prasad C.V.C., and Ogilvie W.W. Angew. Chem., Int. Ed. Engl. 30 (1991) 299
37. Pearson R.G. J. Am. Chem. Soc. 85 (1963) 3533
38. Ho T.-L. Chem. Rev. 75 (1975) 1
39. Hegedus L.L., and McCabe R.W. Catalyst Poisoning (1984), Marcel Dekker, New York, NY
40. Dubois M.R. Chem. Rev. 89 (1989) 1
41. Marécot P., Paraiso E., Dumas J.M., and Barbier J. Appl. Catal. A: Gen. 80 (1992) 79
42. Nishide K., Shigeta Y., Obata K., and Node M. J. Am. Chem. Soc. 118 (1996) 13103
43. Ong B.S. Tetrahedron Lett. 21 (1980) 4225
44. Firouzabadi H., Iranpoor N., and Kohmareh G. Synth. Commun. 33 (2003) 167
45. Srivastava N., and Banik B.K. J. Org. Chem. 68 (2003) 2109
46. Alam M.M., Varala R., and Adapa S.R. Tetrahedron Lett. 44 (2003) 5115
47. Komatsu N., Uda M., and Suzuki H. Synlett (1995) 984
48. Srivastava N., Dasgupta S., and Banik B.K. Tetrahedron Lett. 44 (2003) 1191
49. Garg S.K., Kumar R., and Chakraborti A.K. Tetrahedron Lett. 46 (2005) 1721
50. Anand R.V., Saravanan P., and Singh V.K. Synlett (1999) 415
51. Besra R.C., Rudrawar S., and Chakraborti A.K. Tetrahedron Lett. 46 (2005) 6213
52. Chu C.-M., Huang W.-J., Lu C., Wu P., Liu J.-T., and Yao C.-F. Tetrahedron Lett. 47 (2006) 7375
53. Bandgar B.P., Kamble V.T., and Kulkarni A. Aust. J. Chem. 58 (2005) 607
54. Adibi H., and Jafari H. J. Fluorine Chem. 128 (2007) 679
55. Bandini M., Cozzi P.G., Giacomini M., Melchiorre P., Selva S., and Umani-Ronchi A. J. Org. Chem. 67 (2002) 3700
56. Ceschi M.A., Felix L.D.A., and Peppe C. Tetrahedron Lett. 41 (2000) 9695
57. Muthusamy S., Babu S.A., and Gunanathan C. Tetrahedron 58 (2002) 7897
58. Ranu B.C., Das A., and Samanta S. Synlett (2002) 727
59. Rana K.K., Guin C., Jana S., and Roy S.C. Tetrahedron Lett. 44 (2003) 8597
60. Goswami S., and Maity A.C. Tetrahedron Lett. 49 (2008) 3092
61. Kanemasa S., Oderaotoshi Y., and Wada E. J. Am. Chem. Soc. 121 (1999) 8675
62. Lee W.-Z., Wang T.-L., Tsang H.-S., Liu C.-Y., Chen C.-T., and Kuo T.-S. Organometallics 28 (2009) 652
63. Khan A.T., Mondal E., Sahu P.R., and Islam S. Tetrahedron Lett. 44 (2003) 919
64. Zhang H., Zhang Y., Liu L., Xu H., and Wang Y. Synthesis (2005) 2129
65. De S.K. Adv. Synth. Catal. 347 (2005) 673
66. Aki M.M.A., Sauerland S.J.K., and Koskinen A.M.P. J. Org. Chem. 72 (2007) 5411
67. Kamal A., and Chouhan G. Tetrahedron Lett. 43 (2002) 1347
68. Karimi B., and Ma'mani L. Synthesis (2003) 2503
69. Tseng T.-C., and Wu M.-J. Tetrahedron: Asymmetry 6 (1995) 1633
70. Kumar V., and Dev S. Tetrahedron Lett. 24 (1983) 1289
71. Garg S.K., Kumar R., and Chakraborti A.K. Synlett (2005) 1370
72. Evans D.A., Truesdale L.K., Grimm K.G., and Nesbitt S.L. J. Am. Chem. Soc. 99 (1977) 5009
73. Lipshutz B.H., Lee C.-T., and Servesko J.M. Org. Lett. 9 (2007) 4713
74. Lin Y.-D., Kao J.-Q., and Chen C.-T. Org. Lett. 9 (2007) 5195
75. Weng S.-S., Lin Y.-D., and Chen C.-T. Org. Lett. 8 (2006) 5633
76. Chen C.-T., Weng S.-S., Kao J.-Q., Lin C.-C., and Jan M.-D. Org. Lett. 7 (2005) 3343
77. Chen C.-T., Kuo J.-H., Ku C.-H., Weng S.-S., and Liu C.-Y. J. Org. Chem. 70 (2005) 1328
78. Chen C.-T., Kuo J.-H., Pawar V.D., Munot Y.S., Weng S.-S., Ku C.-H., and Liu C.-Y. J. Org. Chem. 70 (2005) 1188
79. Chen C.-T., Bettigeri S., Weng S.-S., Pawar V.D., Lin Y.-H., Liu C.-Y., and Lee W.-Z. J. Org. Chem. 72 (2007) 8175
80. Pawar V.D., Bettigeri S., Weng S.-S., Kao J.-Q., and Chen C.-T. J. Am. Chem. Soc. 128 (2006) 6308
81. Weng S.-S., Shen M.-W., Kao J.-Q., Munot Y.S., and Chen C.-T. Proc. Natl. Acad. Sci. U.S.A. 103 (2006) 3522
82. Chen C.-T., Lin J.-S., Kuo J.-H., Weng S.-S., Cuo T.-S., Lin Y.-W., Cheng C.-C., Huang Y.-C., Yu J.-K., and Chou P.-T. Org. Lett. 6 (2004) 4471
83. Chen C.-T., Lin Y.-H., and Kuo T.-S. J. Am. Chem. Soc. 130 (2008) 12842
84. 2O, see:. Magnussen M., Brock-Nannestad T., and Bendix J. Acta Crystallogr., Sect. C 63 (2007) m51
85. 2 in catalyzing thioacetalization of aldehydes, see:. De S.K. J. Mol. Catal. A: Chem. 226 (2005) 77
86. Chibnik, S.; Foster, H. M.; Kaufman, H. A.; Glick, L. A. U.S. Patent 3,409,664, 1968.
87. Kilsheimer J.R., Kaufman H.A., Foster H.M., Uriscoll R., Glick L.A., and Napier R.P. J. Agric. Food Chem. 17 (1969) 91
88. Kumar A., Jain N., Rana S., and Chauhan S.M.S. Synlett (2004) 2785
89. Kazahaya K., Tsuji S., and Sato T. Synlett (2004) 1640
90. See Ref. 22b;
91. Saraswathy V.G., and Sankararaman S. J. Org. Chem. 59 (1994) 4665
92. See: Ref. 15b;
93. Fieser L.F. J. Am. Chem. Soc. 76 (1954) 1945
94. Under the same reaction conditions, intermolecular competition between equal molar of benzaldehyde and acetophenone was resulted with only aldehyde protected adduct 5a (94%, 1 h).
95. Gopinath R., Haque S.J., and Patel B.K. J. Org. Chem. 67 (2002) 5842
96. 2 for differential thioacetalization, it was afforded with higher chemical yields (90% and 87%) but lower chemoselectivities (89:11 and 91:9) in shorter reaction times (23 h and 28 h) for 29a/29b and 30a/30b, respectively.
97. Ralls J.W., and Riegel B. J. Am. Chem. Soc. 76 (1954) 4479
98. Sato T., Otera J., and Nozaki H. J. Org. Chem. 58 (1993) 4971
99. See: Ref. 25b.
100. Ellervik U., Jacobsson M., and Ohlsson J. Tetrahedron 61 (2005) 2421
101. Kim K.S., Song Y.H., Lee B.H., and Hahn C.S. J. Org. Chem. 51 (1986) 404
102. Yan M.-C., Chen Y.-N., Wu H.-T., Lin C.-C., Chen C.-T., and Lin C.-C. J. Org. Chem. 72 (2007) 299