Oxidative coupling of diaryldisulfides by MoCl5 to thianthrenes

Chemistry - A European Journal

Volumn 15, Issue 48, 2009, Pages

  Spurg, Anke ^a   Schnakenburg, Gregor ^a   Waldvogel, Siegfried R ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

C c coupling; Cyclization; Heterocycles; Molybdenum; Sulfur

Indexed keywords

C-C COUPLING; CHEMICAL EQUATIONS; HETEROCYCLES; OXIDATIVE COUPLING REACTIONS; OXIDATIVE COUPLINGS;

CHEMICAL BONDS; MOLYBDENUM; SULFUR;

CYCLIZATION;

EID: 72449180392     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200902466     Document Type: Article

References (74)

1. a) G. Bringmann, A. J. P. Mortimer. P.A. Keller. M.J. Gresser, J. Garner, M. Breuning, Angew. Chem. 2005, 117, 5518-5563;
2. Angew. Chem. Int. Ed. 2005, 44, 5384-5427;
3. b) G. Bringmann. C. Günther, M. Ochse. O. Schupp, S. Tasler in Progress in the Chemistry of Organic Natural Products, Vol.80 (Eds.: W. Herz. H. Falk, G. W. Kirby. R. E. Moore), Springer, Wien 2001.
4. a) R. Noyori. Angew. Chem. 2002, 114, 2108-2123;
5. Angew. Chem. int. Ed. 2002, 41, 2008-2022:
6. b) W. S. Knowles. Angew. Chem. 2002. 114, 2096-2107;
7. Angew. Chem. Int. Ed. 2002, 41, 1998-2007.
8. A. C. Grimsdale, K. L. Chan, R. E. Martin, P. G. Jokisz, A. B. Holmes. Chem. Rev. 2009, 109, 897-1091.
9. Metal-Catalyzed Cross Coupling Reactions, Vol.1 (Eds.: A. deMeijere, F. Diederich), Wiley-VCH, Weinheim 2004:
10. Metal-Catalyzed Cross Coupling Reactions, Vol.2 (Eds.: A. de Meijere, F. Diederich). Wiley-VCH, Weinheim 2004.
11. D. Alberico. M. E. Scott, M. Lautens. Chem. Rev. 2007, 107, 174-238.
12. G. Lessene, Ken. S. Feldman in Modern Arene Chemisty (Ed.: D. Aslruc), Wiley-VCH, Weinheim 2002, pp. 479-534.
13. a) I. M. Malkowsky. U. Griesbach, H. Pütler, S. R. Waldvogel, Chem. Eur. J. 2006, 12, 7482-7488;
14. b) A. Kirste. M. Nieger, I. M. Malkowsky, F. Stecker, A. Fischer. S. R. Waldvogel, Chem Eur. J. 2009, 15, 2273-2277.
15. a) S. Cossu, G. Delogu, O. De Lucchi. D. Fabbri, M. P. Fois. Synth. Commun. 1989, 19, 3431-3435;
16. b) T. Nabeshima, A. Sakiyama, A. Yagyu, N. Furukawa, Tetrahedron Lett. 1989, 30, 5287-5288;
17. c) U. K. Bandarage, G. F. Painter, R. A. J. Smith, Tetrahedron: Asymmetry 1995, 6, 295-300.
18. J. Beck, T. Bredow, R. T. Tjahjanlo, Z. Naturforsch. B 2009, 64, 145-152.
19. [K)] a) R. Zieba, C. Desroches, F. Sigala, E. Jeanneau, S. Parola, Tetrahedron Lett. 2007, 48, 5401-5405:
20. b) R. Zieba, C. Desroches, E. Jeanneau, S. Parola. Tetrahedron 2007, 63, 10809-10816.
21. a) D. Casarini, C. Coluccini. L. Lunazzi, A. Mazzanti, J.Org. Chem. 2006, 71, 6248-6250;
22. b) H. Takeuchi, K. Suga, J. Chem. Soc. Perkin Trans. 2 2000, 1803-1808;
23. c) G. Dougherty, P. D. Hammond, J. Am. Chem. Soc. 1935, 57, 117-118.
24. V. I. Stenberg, P. G. Sweeny, Ind. Eng. Chem. Fundam. 1986, 25, 735-741.
25. F. See, R. Budenz, R. D. Flaccus, R. Staab, J. Fluorine Chem. 1978, 12, 437-438.
26. a) L. Benati, P. C. Montevecchi, P. Spagnolo, Chem. Commun. 1980, 715-717;
27. b) A. Albertazzi, R. Leardini, G. F. Pedulli, A. Tundo, G. Zanardit, J.Org. Chem. 1984, 49, 4482-4486.
28. a) S. Ogawa, M. Sugawara, Y. Kawai, S. Niizuma, T. Kimura, R. Sato, Tetrahedron Lett. 1999, 40, 9101-9106;
29. b) N.A.A. Al-Jabar, A. G. Massey, J.Organomet. Chem. 1984, 275, 9-18.
30. S. R. Waldvogel, R. Fröhlich, C. A. Schalley, Angew. Chem. 2000, 112, 2580-2583;
31. Angew. Chem. Int. Ed. 2000, 39, 2472-2475.
32. B. Kramer, A. Averhoff, S. R. Waldvogel, Angew. Chem. 2002, 114, 3103-3104;
33. Angew. Chem. Int. Ed. 2002, 41, 2981-2982.
34. B. Kramer, S. R. Waldvogel, Angew. Chem 2004, 116, 2501-2503;
35. Angew. Chem. Int. Ed. 2004, 43, 2446-2449.
36. S. R. Waldvogel, Synlett 2002, 622-624.
37. S. R. Waldvogel, E. Aits, C. Holst, R. Fröhlich, Chem. Commun. 2002, 1278-1279.
38. B. Kramer, R. Fröhlich, K. Bergander, S. R. Waldvogel, Synthesis 2003, 91-96.
39. B. T. King, J. Kroulik, C. R. Robertson, P. Rempala, C. L. Hilton, J. D. Korinek, L. M. Gortari, J. Org. Chem. 2007, 72, 2279-2288.
40. D. Mirk, A. Willner, R. Fröhlich, S. R. Waldvogel, Adv. Synth. Catal. 2004, 346, 675-681.
41. B. Kramer, R. Fröhlich, S. R. Waldvogel, Eur. J. Org. Chem. 2003, 3549-3554.
42. a) T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, 3rd ed., Wiley, New York, 1999, pp. 487-489;
43. b) P. J. Kocienski, Protecting Groups, 3rd ed., Thieme, Stuttgart, 2004, pp. 380-388.
44. H. Bock, P. Rittmeyer, Phosphorus Sulfur Silicon Relat. Eiern. 1992, 68, 261-291.
45. Melting point differs tremendously: K. Fries, E. Engelbertz, Liebigs Ann. Chem. 1915, 407, 194-228.
46. Melting point differs tremendously: K. Kobayashi, M. Takahashi, H. Kobayashi, J. Chem. Soc. Perkin Trans. 2 1988, 427-430.
47. a) H. Lynton, E. G. Cox, J. Chem. Soc. 1956, 4886-4895;
48. b) I. Rowe, B. Post, Acta Crystallogr. 1956, 9, 827;
49. c) I. Rowe, B. Post, Acta Crystallogr. 1958, 11, 372-374.
50. Angles were determined by calculating the angles between the least-squares planes defined by the two sulphur atoms and the six carbon atoms of the individual phenylene moieties.
51. A. Spurg, S. R. Waldvogel, Synlett 2007, 3042-3044.
52. A. Spurg, S. R. Waldvogel, Eur. J. Org. Chem. 2008, 337-342.
53. D. Mirk, S. R. Waldvogel, Tetrahedron Lett. 2004, 45, 7911-7914.
54. L. Engman, J. Heterocycl. Chem. 1984, 21, 413-416.
55. Extrusion of the sulphur moiety upon conversion to the S-oxides: a) S. Becker, Y. Fort, R. Vanderesse, P. Caubere, Tetrahedron Lett. 1988, 29, 2963-2966;
56. b) J. J. Eisch, K. R. Im, J. Organomet. Chem. 1977, 139, C51-C55;
57. c) J.J. Eisch, L. E. Hallenbeck, K. I. Han, J. Am. Chem. Soc. 1986, 108, 7763-7767;
58. d) H. Suhr, P. Heme, D. Iacocca, M. J. Ropero, Liebigs Ann. Chem. 1980, 441-446;
59. e) H. Gilman, D. R. Swayampati, J. Am. Chem. Soc. 1955, 77, 3387-3389;
60. f) B. Boduszek, H. J. Shine, T. K. Venkatachalam, J.Org. Chem. 1989, 54, 1616-1626.
61. a) For survey: "Diaryldisulfides": O. A. Rakitin, Science of Synthesis, Vol.31 (Ed.: R. Taylor), Thieme, Stuttgart, pp. 1093-1094;
62. b) A. G. M. Barrett, D. Dhanak, G. G. Graboski, S. J. Taylor, Org. Synth. 1990, 68, 8;
63. c) P. D. Senter, J. W. E. Pearce, R. S. Greenfield, J. Org. Chem. 1990, 55, 2975-2978.
64. a) K. Matsumoto, S. Fujie, K. Ueoka, S. Suga, J.-I. Yoshida, Angew. Chem. 2008, 120, 2540-2542;
65. Angew. Chem. Int. Ed. 2008, 47, 2506-2508;
66. b) S. Suga, K. Matsumoto, K. Ueoka, J.-I. Yoshida, J. Am. Chem. Soc. 2006, 128, 7710-7711;
67. c) K. Matsumoto, K. Ueoka, S. Fujie, S. Suga, X Yoshida, Heterocycles 2008, 76, 1103-1119;
68. d) M. Okajima, S. Suga, K. Itami, J. Yoshida, J. Am. Chem. Soc. 2005, 127, 6930-6931;
69. e) T. Maruyama, S. Suga, J. Yoshida, J. Am. Chem. Soc. 2005, 127, 7324-7325;
70. f) T. Maruyama, S. Suga, J. Yoshida, Tetrahedron 2006, 62, 6519-6525;
71. g) J. Yoshida, S. Suga, Chem. Eur. J. 2002, 8, 2650-2658.
72. A. S. Gybin, W. A. Smit, V. S. Bogdanov, Tetrahedron Lett. 1980, 21, 383-386.
73. a) B. Miller, C.H. Han, J.Org. Chem. 1971, 36, 1513-1519;
74. b) T. Fujisawa, N. Ohtsuka, G. Tsuchihashi, Bull. Chem. Soc. Jpn. 1970, 43, 1189-1196.