Highly regioselective double hydrothiolation of terminal acetylenes with thiols catalyzed by palladium diacetate

Bulletin of the Chemical Society of Japan

Volumn 84, Issue 4, 2011, Pages 413-415

  Mitamura, Takenori ^a   Daitou, Masayuki ^a   Nomoto, Akihiro ^a   Ogawa, Akiya ^a  

^a Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GOOD YIELD; HYDROTHIOLATION; REGIO-SELECTIVE; TERMINAL ACETYLENE;

ACETYLENE; REGIOSELECTIVITY;

LIGHTING;

EID: 79954459217     PISSN: 00092673     EISSN: 13480634     Source Type: Journal    
DOI: 10.1246/bcsj.20100311     Document Type: Article

References (55)

1. a) T. Wirth, Angew. Chem., Int. Ed. 2000, 39, 3740.
2. b) G. Mugesh, W.-W. du Mont, H. Sies, Chem. Rev. 2001, 101, 2125.
3. c) C. W. Nogueira, G. Zeni, J. B. T. Rocha, Chem. Rev. 2004, 104, 6255.
4. d) G. Zeni, D. S. Lüdtke, R. B. Panatieri, A. L. Braga, Chem. Rev. 2006, 106, 1032.
5. e) J. F. Hartwig, Acc. Chem. Res. 2008, 41, 1534.
6. f) G. Perin, E. J. Lenardão, R. G. Jacob, R. B. Panatieri, Chem. Rev. 2009, 109, 1277.
7. g) Organosulfur Chemistry I in Topics in Current Chemistry, ed. by P. C. B. Page, Springer, Berlin, 1999, Vol. 204. doi:10.1007/3-540-48956-8
8. h) Organosulfur Chemistry II in Topics in Current Chemistry, ed. by P. C. B. Page, Springer, Berlin, 1999, Vol. 205. doi:10.1007/3-540-48986-X
9. a) A. Ogawa, J. Organomet. Chem. 2000, 611, 463.
10. b) T. Kondo, T. Mitsudo, Chem. Rev. 2000, 100, 3205.
11. c) F. Alonso, I. P. Beletskaya, M. Yus, Chem. Rev. 2004, 104, 3079.
12. d) I. Beletskaya, C. Moberg, Chem. Rev. 2006, 106, 2320.
13. e) H. Kuniyasu, N. Kambe, Chem. Lett. 2006, 35, 1320.
14. a) H. Kuniyasu, A. Ogawa, S. Miyazaki, I. Ryu, N. Kambe, N. Sonoda, J. Am. Chem. Soc. 1991, 113, 9796.
15. b) H. Kuniyasu, A. Ogawa, K. Sato, I. Ryu, N. Kambe, N. Sonoda, J. Am. Chem. Soc. 1992, 114, 5902.
16. c) A. Ogawa, T. Ikeda, K. Kimura, T. Hirao, J. Am. Chem. Soc. 1999, 121, 5108.
17. a) A. Ogawa, J. Kawakami, N. Sonoda, T. Hirao, J. Org. Chem. 1996, 61, 4161.
18. b) S. Kodama, E. Nishinaka, A. Nomoto, M. Sonoda, A. Ogawa, Tetrahedron Lett. 2007, 48, 6312.
19. For recent advances in bisthiolation, see: a) T. Kondo, S. Uenoyama, K. Fujita, T. Mitsudo, J. Am. Chem. Soc. 1999, 121, 482.
20. b) M. Arisawa, M. Yamaguchi, Org. Lett. 2001, 3, 763.
21. c) V. P. Ananikov, M. A. Kabeshov, I. P. Beletskaya, G. G. Aleksandrov, I. L. Eremenko, J. Organomet. Chem. 2003, 687, 451.
22. d) V. P. Ananikov, I. P. Beletskaya, G. G. Aleksandrov, I. L. Eremenko, Organometallics 2003, 22, 1414.
23. e) S. Usugi, H. Yorimitsu, H. Shinokubo, K. Oshima, Org. Lett. 2004, 6, 601.
24. f) V. P. Ananikov, I. P. Beletskaya, Org. Biomol. Chem. 2004, 2, 284.
25. g) V. P. Ananikov, M. A. Kabeshov, I. P. Beletskaya, Synlett 2005, 1015.
26. h) V. P. Ananikov, M. A. Kabeshov, I. P. Beletskaya, V. N. Khrustalev, M. Y. Antipin, Organometallics 2005, 24, 1275.
27. i) M. Arisawa, K. Fujimoto, S. Morinaka, M. Yamaguchi, J. Am. Chem. Soc. 2005, 127, 12226.
28. j) I. P. Beletskaya, V. P. Ananikov, Pure Appl. Chem. 2007, 79, 1041.
29. k) I. P. Beletskaya, V. P. Ananikov, Eur. J. Org. Chem. 2007, 3431.
30. l) M. Cai, Y. Wang, W. Hao, Green Chem. 2007, 9, 1180.
31. m) V. P. Ananikov, K. A. Gayduk, I. P. Beletskaya, V. N. Khrustalev, M. Y. Antipin, Chem. - Eur. J. 2008, 14, 2420.
32. n) V. P. Ananikov, N. V. Orlov, M. A. Kabeshov, I. P. Beletskaya, Z. A. Starikova, Organometallics 2008, 27, 4056.
33. o) H. Kuniyasu, K. Takekawa, F. Yamashita, K. Miyafuji, S. Asano, Y. Takai, A. Ohtaka, A. Tanaka, K. Sugoh, H. Kurosawa, N. Kambe, Organometallics 2008, 27, 4788.
34. p) M. Wang, L. Cheng, B. Hong, Z. Wu, Organometallics 2009, 28, 1506.
35. q) N. Taniguchi, Tetrahedron 2009, 65, 2782.
36. r) Y. Nishiyama, H. Ohnishi, Y. Koguma, Bull. Chem. Soc. Jpn. 2009, 82, 1170.
37. s) A. Nomoto, G. Shiino, A. Ogawa, Res. Chem. Intermed. 2009, 35, 965.
38. t) V. P. Ananikov, K. A. Gayduk, I. P. Beletskaya, V. N. Khrustalev, M. Y. Antipin, Eur. J. Inorg. Chem. 2009, 1149.
39. u) V. P. Ananikov, K. A. Gayduk, N. V. Orlov, I. P. Beletskaya, V. N. Khrustalev, M. Y. Antipin, Chem. - Eur. J. 2010, 16, 2063.
40. For recent advances in hydrothiolation, see: a) W.-J. Xiao, H. Alper, J. Org. Chem. 2001, 66, 6229.
41. b) I. Kamiya, E. Nishinaka, A. Ogawa, J. Org. Chem. 2005, 70, 696.
42. c) V. P. Ananikov, D. A. Malyshev, I. P. Beletskaya, G. G. Aleksandrov, I. L. Eremenko, Adv. Synth. Catal. 2005, 347, 1993.
43. d) C. Cao, L. R. Fraser, J. A. Love, J. Am. Chem. Soc. 2005, 127, 17614.
44. e) V. P. Ananikov, N. V. Orlov, I. P. Beletskaya, Organometallics 2006, 25, 1970.
45. f) D. A. Malyshev, N. M. Scott, N. Marion, E. D. Stevens, V. P. Ananikov, I. P. Beletskaya, S. P. Nolan, Organometallics 2006, 25, 4462.
46. g) V. P. Ananikov, N. V. Orlov, I. P. Beletskaya, V. N. Khrustalev, M. Y. Antipin, T. V. Timofeeva, J. Am. Chem. Soc. 2007, 129, 7252.
47. h) A. Kondoh, H. Yorimitsu, K. Oshima, Org. Lett. 2007, 9, 1383.
48. i) L. R. Fraser, J. Bird, Q. Wu, C. Cao, B. O. Patrick, J. A. Love, Organometallics 2007, 26, 5602.
49. j) S. Shoai, P. Bichler, B. Kang, H. Buckley, J. A. Love, Organometallics 2007, 26, 5778.
50. k) S. Kodama, A. Nomoto, M. Kajitani, E. Nishinaka, M. Sonoda, A. Ogawa, J. Sulfur Chem. 2009, 30, 309.
51. l) J. Yang, A. Sabarre, L. R. Fraser, B. O. Patrick, J. A. Love, J. Org. Chem. 2009, 74, 182.
52. m) A. Corma, C. González-Arellano, M. Iglesias, F. Sánchez, Appl. Catal., A 2010, 375, 49.
53. 3-catalyzed addition of thiols to acetylenes, leading to dithioketals, see: J. S. Yadav, B. V. Subba Reddy, A. Raju, K. Ravindar, G. Baishya, Chem. Lett. 2007, 36, 1474.
54. 2O (ca. 0.1 mmol) in THF was conducted, a complex mixture of 1,1-bis(phen-ylsulfanyl) ethylbenzene, 2-phenylsulfanylstyrene, and 1-phenylsulfanyl-styrene was obtained.
55. For the monohydrothiolation using deuterated thiol, see Ref. 3b.