Homogeneous nickel catalysts for the selective transfer of a single arylthio group in the catalytic hydrothiolation of alkynes

Organometallics

Volumn 25, Issue 19, 2006, Pages 4462-4470

  Malyshev, Denis A ^a,b   Scott, Natalie M ^a   Marion, Nicolas ^a   Stevens, Edwin D ^a   Ananikov, Valentine P ^b   Beletskaya, Irina P ^c   Nolan, Steven P ^a  

^a UNIVERSITY OF NEW ORLEANS   (United States)

^b N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^c MOSCOW STATE UNIVERSITY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLTHIO GROUP; PROTONOLYSIS; REGIOSELECTIVE HYDROTHIOLATION; SELECTIVE TRANSFER;

ADDITION REACTIONS; CATALYSTS; NICKEL; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); X RAY ANALYSIS;

HYDROCARBONS;

EID: 33748807078     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om060302v     Document Type: Article

References (56)

1. (a) Truce, W. E.; Hill, H. E.; Boudakian, M. M. J. Am. Chem. Soc. 1956, 78, 2756-2759.
2. (b) Truce, W. E.; Heine, R. F. J. Am. Chem. Soc. 1957, 79, 5311-5313.
3. (c) Griesbaum, K. Angew. Chem., Int. Ed. Engl. 1970, 9, 273-287.
4. (d) Trofimov, B. A. Russ. Chem. Rev. 1981, 50, 138-150.
5. (e) Ichinose, Y.; Wakamatsu, K.; Nozaki, K.; Birbaum, J.-L.; Oshima, K.; Utimoto, K. Chem. Lett. 1987, 1647-1650.
6. (f) Back, T. G.; Krishna, M. V. J. Org. Chem. 1988, 53, 2533-2536.
7. (g) Benati, L.; Capella, L.; Montevecchi, P. C.; Spagnolo, P. J. Chem. Soc., Perkin Trans. 1995, 1035-1038.
8. (h) Trofimov, B. A. Curr. Org. Chem. 2002, 6, 1121-1162.
9. (a) Perspectives in Organic Chemistry of Sulfur, Elsevier: Amsterdam, 1987.
10. (b) Sulfur Reagents in Organic Synthesis; Academic Press: New York, 1994.
11. (c) Waters, M. S.; Snelgrove, K.; Maligres, P. Org. Synth. 2003, 80, 190-194.
12. (a) Kondo, T.; Mitsudo, T. Chem. Rev. 2000, 100, 3205-3220.
13. (b) Ogawa, A. J. Organomet. Chem. 2000, 611, 463-474.
14. (c) Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079-3159.
15. (d) Beller, M.; Seayad, J.; Tillack, A.; Jiao, H. Angew. Chem., Int. Ed. 2004, 43, 3368-3398.
16. (a) Kuniyasu, H.; Ogawa, A.; Sato, K.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 5902-5903.
17. (b) Ogawa, A.; Ikeda, T.; Kimura, K.; Hirao, T. J. Am. Chem. Soc. 1999, 121, 5108-5114.
18. Ananikov, V. P.; Malyshev, D. A.; Beletskaya, I. P.; Aleksandrov, G. G.; Eremenko, I. L. Adv. Synth. Catal. 2005, 347, 1993-2001.
19. (a) Kanemasa, S.; Oderaotoshi, Y.; Wada, E. J. Am. Chem. Soc. 1999, 121, 8675-8676.
20. (b) Shulyupin, M. O.; Kazankova, M. A.; Beletskaya, I. P. Org. Lett. 2002, 4, 761-763.
21. (c) Kazankova, M. A.; Shulyupin, M. O.; Beletskaya, I. P. Synlett 2003, 14, 2155-2158.
22. (d) Han, L.-B.; Zhang, C.; Yazawa, H.; Shimada, S. J. Am. Chem. Soc. 2004, 126, 5080-5081.
23. (e) Ribiere, P.; Bravo-Altamirano, K.; Antczak, M. I.; Hawkins, J. D.; Montchamp, J.-L. J. Org. Chem. 2005, 70, 4064-4072.
24. Ananikov, V. P.; Orlov, N. V.; Beletskaya, I. P. Organometallics 2006, 25, 1970-1977.
25. (a) Lee, H. M.; Jiang, T.; Stevens, E. D.; Nolan, S. P. Organometallics 2001, 20, 1255-1258.
26. (b) Hillier, A. C.; Lee, H. M.; Stevens, E. D.; Nolan, S. P. Organometallics 2001, 20, 4246-4252.
27. (c) Viciu, M. S.; Nolan, S. P. Top. Organomet. Chem. 2005, 14, 241-278.
28. (d) Dorta, R.; Stevens, E. D.; Scott, N. M.; Costabile, C.; Cavallo, L.; Hoff, C. D.; Nolan, S. P. J. Am. Chem. Soc. 2005, 127, 2485-2495.
29. (a) Weskamp, T.; Schattenmann, W. C.; Spiegler, M.; Herrmann, W. A. Angew. Chem., Int. Ed. 1998, 37, 2490-2493.
30. (b) Huang, J.; Stevens, E. D.; Nolan, S. P.; Petersen, J. L. J. Am. Chem. Soc. 1999, 121, 2674-2678.
31. (c) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
32. (d) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3013-3043.
33. (e) Jafarpour, L.; Nolan, S. P. J. Organomet. Chem. 2001, 617, 17-27.
34. (f) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29.
35. (g) Grubbs, R. H. Handbook of Metathesis; Wiley-VCH: New York, 2003.
36. Selectivity of the catalytic reaction was determined as a (1+4)/ (2+3) ratio (see Scheme 1).
37. The plot of observed yield vs time and calculated rate constants are given in the Supporting Information.
38. 8-toluene, 400 MHz, δ (ppm)): 5.20 (s, 1H), 5.28 (s, 1H), 6.20 (s, 1H); see: (a) Guittet, E.; Julia, S. Synth. Comm. 1981, 11, 697-708.
39. (b) Oida, T.; Tanimoto, S.; Ikehira, H.; Okano, M. Bull. Chem. Soc. Jpn. 1983, 56, 959-960.
40. (c) Jacobs, T. L.; Mihailovsky, A. Tetrahedron Lett. 1967, 27, 2607-2611.
41. (d) Blatcher, P.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1985, 1055-1065.
42. (e) Ager, D. J.; East, M. B. J. Org. Chem. 1986, 51, 3983-3992.
43. 2).
44. Abernethy, C. D.; Cowley, A. H.; Jones, R. A. J. Organomet. Chem. 2000, 596, 3-5.
45. Kelly, R. A., III; Scott, N. M.; Díez-González, S.; Stevens, E. D.; Nolan, S. P. Organometallics 2005, 24, 3442-3447.
46. Taube, R.; Steinborn, D.; Hobold, W. J. Organomet. Chem. 1985, 284, 385-394.
47. In addition to disulfides, GC-MS analysis revealed the presence of two other compounds, with m/e = 204 and 336 (see Experimental Section for details), which will be discussed later.
48. 3N additive.
49. For examples of transition metal catalyzed C-S bond activation, see: (a) Kuniyasu, H.; Ohtaka, A.; Nakazono, T.; Kinomoto, M.; Kurosawa, H. J. Am. Chem. Soc. 2000, 122, 2375-2376.
50. (b) Egi, M.; Liebeskind, L. S. Org. Lett. 2003,5, 801-802.
51. (c) Kusturin, C.; Liebeskind, L. S.; Rahman, H.; Sample, K.; Schweitzer, B.; Srogl, J.; Neumann, W. L. Org. Lett. 2003, 5, 4349-4352.
52. (d) Fausett, B. W.; Liebeskind, L. S. J. Org. Chem. 2005, 70, 4851-4853.
53. An example of transition metal promoted sulfur atom transfer to the triphenylphosphine ligand has been recently reported; see: Ananikov, V. P.; Orlov, N. V.; Beletskaya, I. P. Russ. Chem. Bull., Int. Ed. 2005, 54, 576-587.
54. 4SH (Table 6, entries 3-6) addition to alkynes.
55. Ogawa, A.; Kawakami, J.; Sonoda, N.; Hirao, T. J. Org. Chem. 1996, 61, 4161-4163.
56. Yus, M.; Gutierrez, F. A.; Foubelo, F. Tetrahedron 2001, 57, 4411-4422.