Conversion of alcohols to alkyl aryl sulfides by a new type of oxidation-reduction condensation using phenyl diphenylphosphinite

Bulletin of the Chemical Society of Japan

Volumn 82, Issue 3, 2009, Pages 381-392

  Kuroda, Kiichi ^a   Maruyama, Yuji ^a   Hayashi, Yujiro ^a   Mukaiyama, Teruaki ^b  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

^b KITASATO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARYL SULFIDES; BENZOQUINONE; BENZOTHIAZOLE; CHIRAL SULFIDES; INVERSION OF CONFIGURATIONS; NEUTRAL CONDITIONS; TERTIARY ALCOHOLS;

ALKYLATION; CONDENSATION; SULFUR COMPOUNDS;

OXIDATION;

EID: 63149135434     PISSN: 00092673     EISSN: 13480634     Source Type: Journal    
DOI: 10.1246/bcsj.82.381     Document Type: Article

References (88)

1. a) D. J. Procter, J. Chem. Soc., Perkin Trans. 1 2001, 335.
2. b) D. J. Procter, J. Chem. Soc., Perkin Trans. 1 2000, 835.
3. c) D. J. Procter, J. Chem. Soc., Perkin Trans. 1 1999, 641.
4. d) C. P. Baird, C. M. Rayner, J. Chem. Soc., Perkin Trans. 1 1998, 1973.
5. a) N. A. Sasaki, C. Hashimoto, P. Potier, Tetrahedron Lett. 1987, 28, 6069.
6. b) J. Yin, C. Pidgeon, Tetrahedron Lett. 1997, 38, 5953.
7. c) S. Yunoki, K. Takimiya, Y. Aso, T. Otsubo, Tetrahedron Lett. 1997, 38, 3017.
8. d) P. J. Brown, D. A. Winegar, K. D. Plunket, L. B. Moore, M. C. Lewis, J. G. Wilson, S. S. Sundseth, C. S. Koble, Z. Wu, J. M. Chapman, J. M. Lehmann, S. A. Kliewer, T. M. Willson, J. Med. Chem. 1999, 42, 3785.
9. a) F. Y. Kwong, S. L. Buchwald, Org. Lett. 2002, 4, 3517.
10. b) C. G. Bates, R. K. Gujadhur, D. Venkataraman, Org. Lett. 2002, 4, 2803.
11. c) C. Savarin, J. Srogl, L. S. Liebeskind, Org. Lett. 2002, 4, 4309.
12. d) P. S. Herradura, K. A. Pendola, R. K. Guy, Org. Lett. 2000, 2, 2019.
13. e) J. Ham, I. Yang, H. Kang, J. Org. Chem. 2004, 69, 3236.
14. f) J. S. Bradshaw, J. A. South, R. H. Hales, J. Org. Chem. 1972, 37, 2381.
15. g) M. T. Martin, A. M. Thomas, D. G. York, Tetrahedron Lett. 2002, 43, 2145.
16. T. Kondo, T. Mitsudo, Chem. Rev. 2000, 100, 3205.
17. a) T. Mukaiyama, I. Kuwajima, Z. Suzuki, J. Org. Chem. 1963, 28, 2024.
18. b) T. Mukaiyama, R. Matsueda, M. Suzuki, Tetrahedron Lett. 1970, 11, 1901.
19. c) T. Mukaiyama, Angew. Chem., Int. Ed. Engl. 1976, 15, 94.
20. For reviews of the Mitsunobu reaction, see: a) O. Mitsunobu, Synthesis 1981, 1.
21. b) D. L. Hughes, Org. React. 1992, 42, 335.
22. c) R. Dembinski, Eur. J. Org. Chem. 2004, 2763.
23. d) T. Y. S. But, P. H. Toy, Chem. Asian J. 2007, 2, 1340.
24. E. J. Corey, K. A. Cimprich, Tetrahedron Lett. 1992, 33, 4099.
25. a) D. H. Valentine, J. H. Hillhouse, Synthesis 2003, 317.
26. b) J. Skarżewski, A. Gupta, E. Wojaczyñska, R. Siedlecka, Synlett 2003, 1615.
27. c) H. Kotsuki, K. Matsumoto, H. Nishizawa, Tetrahedron Lett. 1991, 32, 4155.
28. d) I. Nakagawa, K. Aki, T. Hata, J. Chem. Soc., Perkin Trans. 1 1983, 1315.
29. e) I. Nakagawa, T. Hata, Tetrahedron Lett. 1975, 16, 1409.
30. f) K. A. M. Walker, Tetrahedron Lett. 1977, 18, 4475.
31. For other methods for preparation of alkyl aryl sulfides from alcohols, see: a) S.-C. Tsay, L. C. Lin, P. A. Furth, C. C. Shum, D. B. King, S. F. Yu, B.-L. Chen, J. R. Hwu, Synthesis 1993, 329.
32. b) Y. Guindon, R. Frenette, R. Fortin, J. Rokach, J. Org. Chem. 1983, 48, 1357.
33. c) Y. Kawano, N. Kaneko, T. Mukaiyama, Chem. Lett. 2005, 34, 1612.
34. For the synthesis of chiral building blocks possessing sulfur-containing quaternary carbons, see: a) B. Strijtveen, R. M. Kellogg, Tetrahedron 1987, 43, 5039.
35. b) O. Stratmann, B. Kaiser, R. Fröhlich, O. Meyer, D. Hoppe, Chem.-Eur. J. 2001, 7, 423.
36. c) F. Marr, D. Hoppe, Org. Lett. 2002, 4, 4217.
37. d) F. Marr, R. Fröhlich, D. Hoppe, Org. Lett. 1999, 1, 2081.
38. e) J. M. McFadden, G. L. Frehywot, C. A. Townsend, Org. Lett. 2002, 4, 3859.
39. f) X. Zhang, Z. Qu, Z. Ma, W. Shi, X. Jin, J. Wang, J. Org. Chem. 2002, 67, 5621.
40. N2 displacement at a quaternary center with various nucleophiles, see: a) Y.-J. Shi, D. L. Hughes, J. M. McNamara, Tetrahedron Lett. 2003, 44, 3609.
41. b) A. Avenoza, J. H. Busto, F. Corzana, G. Jiménez-Osés, J. M. Peregrina, Chem. Commun. 2004, 980.
42. c) T. Kitazume, T Sato, T. Kobayashi, J. T. Lin, J. Org. Chem. 1986, 51, 1003.
43. d) N. D. Smith, M. Goodman, Org. Lett. 2003, 5, 1035.
44. e) F. Effenberger, S. Gaupp, Tetrahedron: Asymmetry 1999, 10, 1765.
45. f) J. Wachtmeister, A. Mühlman, B. Classon, B. Samuelsson, Tetrahedron 1999, 55, 10761.
46. g) D. F. Taber, Y. He, M. Xu, J. Am. Chem. Soc. 2004, 126, 13900.
47. h) Y. Masaki, H. Arasaki, M. Iwata, Chem. Lett. 2003, 32, 4.
48. For reviews of oxidation-reduction condensation, see: a) T Mukaiyama, H. Yamabe, Chem. Lett. 2007, 36, 1.
49. b) T. Mukaiyama, K. Ikegai, H. Aoki, W. Pluempanupat, K. Masutani, Proc Jpn. Acad., Ser. B 2005, 81, 103.
50. c) T. Mukaiyama, Angew. Chem., Int. Ed. 2004, 43, 5590.
51. For carbon-oxygen bond formation reactions, see: a) T. Mukaiyama, T. Shintou, K. Fukumoto, J. Am. Chem. Soc. 2003, 125, 10538.
52. b) T. Shintou, K. Fukumoto, T. Mukaiyama, Bull. Chem. Soc. Jpn. 2004, 77, 1569.
53. c) T. Shintou, W. Kikuchi, T. Mukaiyama, Bull. Chem. Soc. Jpn. 2003, 76, 1645.
54. d) T. Shintou, T. Mukaiyama, J. Am. Chem. Soc. 2004, 126, 7359.
55. For carbon-nitrogen bond formation reactions, see: a) K. Kuroda, Y. Hayashi, T. Mukaiyama, Tetrahedron 2007, 63, 6358.
56. b) K. Kuroda, N. Kaneko, Y. Hayashi, T. Mukaiyama, Chem. Lett. 2006, 35, 1432.
57. c) H. Aoki, T. Mukaiyama, Chem. Lett. 2006, 35, 456.
58. d) H. Aoki, K. Kuroda, T. Mukaiyama, Chem. Lett. 2005, 34, 1266.
59. e) T. Mukaiyama, K. Kuroda, H. Aoki, Chem. Lett. 2005, 34, 1644.
60. f) T. Mukaiyama, H. Aoki, Chem. Lett. 2005, 34, 142.
61. For cyanation and isocyanation, see: a) K. Masutani, T. Minowa, Y. Hagiwara, T. Mukaiyama, Bull. Chem. Soc. Jpn. 2006, 79, 1106.
62. b) T. Mukaiyama, K. Masutani, Y. Hagiwara, Chem. Lett. 2004, 33, 1192.
63. c) K. Masutani, T. Minowa, T. Mukaiyama, Chem. Lett. 2005, 34, 1124.
64. a) K. Ikegai, W. Pluempanupat, T. Mukaiyama, Bull. Chem. Soc. Jpn. 2006, 79, 780.
65. b) K. Ikegai, W. Pluempanupat, T. Mukaiyama, Chem. Lett. 2005, 34, 638.
66. c) T. Mukaiyama, K. Ikegai, Chem. Lett. 2004, 33, 1522.
67. K. Kuroda, Y. Hayashi, T. Mukaiyama, Chem. Lett. 2008, 37, 592.
68. K. Kuroda, Y. Maruyama, Y. Hayashi, T. Mukaiyama, Chem. Lett. 2008, 37, 836.
69. a) F. G. Bordwell, D. L. Hughes, J. Org. Chem. 1982, 47, 3224.
70. b) T. N. Nenasheva, G. A. Sal'nikova, Zh. Org. Khim 1979, 15, 835.
71. c) J. Courtot-Coupez, M. Le Démézet, Bull. Soe Chim. Fr. 1969, 1033.
72. a) D. L. Hughes, R. A. Reamer, J. Org. Chem. 1996, 61, 2967.
73. b) J. A. Dodge, J. I. Trujillo, M. Presnell, J. Org. Chem. 1994, 59, 234.
74. 12b,16a
75. For a review of organic azides, see: S. Bräse, C. Gil, K. Knepper, V. Zimmermann, Angew. Chem., Int. Ed. 2005, 44, 5188.
76. a) H. Staudinger, J. Meyer, Helv. Chim. Acta 1919, 2, 635.
77. b) Y. G. Gololobov, L. F. Kasukhin, Tetrahedron 1992, 48, 1353.
78. a) P. Molina, M. J. Vilaplana, Synthesis 1994, 1197.
79. b) P. M. Fresneda, P. Molina, Synlett 2004, 1.
80. c) S. Eguchi, Arkivoc 2005, Part ii, 98.
81. d) F. Palacios, C. Alonso, D. Aparicio, G. Rubiales, J. M. de los Santos, Tetrahedron 2007, 63, 523.
82. e) E. Saxon, C. R. Bertozzi, Science 2000, 287, 2007.
83. f) E. Saxon, S. J. Luchansky, H. C. Hang, C. Yu, S. C. Lee, C. R. Bertozzi, J. Am. Chem. Soc. 2002, 124, 14893.
84. g) M. Köhn, R. Breinbauer, Angew. Chem., Int. Ed. 2004, 43, 3106.
85. S. Torii, H. Okumoto, M. Fujikawa, M. A. Rashid, Chem. Express 1992, 7, 933.
86. 2 was very slow, an iminophosphorane was not formed efficiently. Thus, it is proven that alkyl azides such as ethyl azidoacetate or benzyl azide are a suitable oxidant.
87. a value such as benzenethiol or 4-methoxybenzenethiol was used. This indicates that the basicity of iminophosphorane is lower than that of phenoxide anion of intermediate A (Scheme 2). On the other hand, reaction of BtzSH with tertiary alcohol Ir gave the desired sulfide along with undesired olefins. Since the yield of the desired product obtained by using an azide is higher than that using a benzoquinone derivative, the reaction using an azide might suppress undesired side reactions such as competitive E2 elimination caused by the iminophosphorane while the reaction using a benzoquinone derivative might promote E2 elimination caused by the phenoxide anion. Thus, the reaction using an azide proceeds under milder conditions to afford the desired product in higher yield.
88. B. Jiang, Z. Chen, X. Tang, Org. Lett. 2002, 4, 3451.