Palladium-catalyzed thiocarbonylation of iodoarenes with thiols in phosphonium salt ionic liquids

Journal of Organic Chemistry

Volumn 73, Issue 9, 2008, Pages 3530-3534

  Cao, Hong ^a   McNamee, Laura ^a   Alper, Howard ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYLATION; CATALYSIS; IONIC LIQUIDS; PALLADIUM; REACTION KINETICS;

PHOSPHONIUM SALTS; THIOESTERS;

OLEFINS;

IONIC LIQUID; PALLADIUM; PHOSPHATE; PHOSPHONIUM DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; THIOESTER; THIOL DERIVATIVE;

ARTICLE; CARBONYLATION; CATALYSIS; CATALYST;

EID: 43449133006     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800287s     Document Type: Article

References (101)

1. (a) Colquhoun, H. M.; Thompson, D. J.; Twigg, M. V. Carbony-lation: Direct Synthesis of Carbonyl Compounds; Plenum Press: New York, 1991.
2. (b) Tsuji, J. Palladium Reagents and Catalysts; Wiley: New York, 1995.
3. (c) Khumtaveeporn, K.; Alper, H. Acc. Chem. Res. 1995, 28, 414.
4. (d) Ishii, Y.; Gao, C.; Iwasaki, M.; Hidai, M. J. Org. Chem. 1993, 58, 6818.
5. (e) Duprat, S.; Deweerdt, H.; Jenck, J.; Kalck, P. J. Mol. Catal. 1993, 80, L9.
6. (f) Tsuji, J.; Mandai, T. Angew. Chem., Int. Ed. Engl. 1995, 3, 4-2589.
7. (g) Piotti, M. E.; Alper, H. J. Org. Chem. 1997, 62, 8484.
8. (h) Zhu, J.; Lu, X. Tetrahedron Lett. 1987, 28, 1987.
9. (i) Zhu, J.; Lu, X. Chem. Commun. 1987, 1318.
10. (j) Marshall, J. A.; Wolf, M. A. J. Org. Chem. 1996, 61, 3238.
11. (k) Kimura, M.; Wakamiya, Y.; Horino, Y.; Tamaru, Y. Tetrahedron Lett. 1997, 38, 3963.
12. (l) Imada, Y.; Alper, H. J. Org. Chem. 1996, 61, 6766.
13. (m) Ito, Y.; Sawamura, M.; Matsuoka, M.; Mastsumoto, Y.; Hayashi, T. Tetrahedron Lett. 1987, 28, 4849.
14. (n) Lu, X.; Jiang, X. J. Organomet. Chem. 1989, 359, 139.
15. (o) Tsuji, J.; Watanabe, H.; Minami, I.; Shimizu, I. J. Am. Chem. Soc. 1985, 107, 2196.
16. (p) Tamaru, Y.; Goto, S.; Tanaka, A.; Shimizu, M.; Kimura, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 878.
17. (q) Bienayme, H. Tetrahedron Lett. 1994, 35, 7387.
18. (r) Tamaru, Y.; Yasui, K.; Takanabe, H.; Tanaka, S.; Fugami, K. Angew. Chem., Int. Ed. Engl. 1992, 31, 645.
19. (s) Luong, T. J.; Linstrumelle, G. Tetrahedron Lett. 1980, 21, 5019.
20. (t) Tseng, H. R.; Luh, T. Y. J. Org. Chem. 1996, 61, 8685.
21. (u) Keinan, E.; Bosch, E. J. Org. Chem. 1986, 51, 4006.
22. (v) Moriya, T.; Miyaura, N.; Suzuki, A. Synlett 1994, n/a, 149.
23. (w) Mandai, T.; Nakata, T.; Murayama, H.; Yamaoki, H.; Ogawa, M.; Kawada, M.; Tsuji, J. J. Organomet. Chem. 1991, 417, 305.
24. (a) Dong, C.; Alper, H. J. Org. Chem. 2004, 69, 5011.
25. (b) Matsushima, Y.; Onitsuka, K.; Takahashi, S. Organometallics 2004, 15, 35.
26. (c) Soderberg, B. C. G. Coord. Chem. Rev. 2003, 247, 79.
27. (d) von Seebach, M.; Grigg, R.; de Meijere, A. Eur. J. Org. Chem. 2002, 19, 3268,
28. (e) Costa, M.; Della Ca, N.; Gabriele, B.; Massera, C.; Salerno, G.; Soliani, M. J. Org. Chem. 2004, 69, 2469.
29. (f) Wu, M. S.; Rayabarapu, D. K.; Cheng, C. H. J. Am. Chem. Soc. 2003, 125, 12426.
30. (g) Yang, F. Y.; Shanmugasundaram, M.; Chuang, S. Y.; Ku, P.-J.; Wu, M. Y.; Cheng, C. H. J. Am. Chem. Soc. 2003, 125, 12576.
31. (h) Zweni, P. P.; Alper, H. Adv. Synth. Catal. 2004, 346, 849.
32. (i) Lu, S. M.; Alper, H. J. Org. Chem. 2004, 69, 3558.
33. (a) Dubois, M. R. Chem. Rev. 1989, 89, 1.
34. (b) Roberto, A. S. D. Organometallic Modeling of the Hydrosulfurization and Hydrodenitrogenation Reaction; Kluwer Academic: Dordrecht, 2002.
35. (c) Weber, T.; Prins, R.; Santen, R. A. Transition Metal Sulphides Chemistry and Catalysis; Kluwer Academic: Dordrecht, 1997.
36. (a) Hegedus, L. L.; McCable, R. W. Catalyst Poisoning; Marcel Dekker: New York, 1984.
37. (b) Hutton, A. T. In Comprehensive Coordination Chemistry; Wilkinson, G., Gillard, R. D., McCleverty, J. A., Eds.; Pergamon Press: Oxford, U. K., 1984; Vol. 5, p 1151.
38. (c) Stiefel, E. I.; Matsumoto, K. Transition Metal Sulfur Chemistry: Biological and Industrial Significance; American Chemical Society: Washington, DC, 1996.
39. (a) Shim, S. C.; Antebi, S.; Alper, H. J. Org. Chem. 1985, 50, 147.
40. (b) Antebi, S.; Alper, H. Tetrahedron Lett. 1985, 26, 2609.
41. (c) Antebi, S.; Alper, H. Tetrahedron Lett. 1985, 26, 1935.
42. (d) Ogawa, A.; Takeba, M.; Kawakami, J.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1995, 117, 7564.
43. For the palladium-catalyzed thiocarbonylation, see: (e) Xiao, W.-J.; Alper, H. J. Org. Chem. 1997, 62, 3422.
44. (f) Xiao, W.-J.; Vasapollo, G.; Alper, H. J. Org. Chem. 1998, 63, 2609.
45. (g) Xiao, W.-J.; Alper, H. J. Org. Chem. 1998, 63, 7939.
46. (h) Xiao, W.-J.; Vasapollo, G.; Alper, H. J. Org. Chem. 1999, 64, 2080.
47. (i) Xiao, W.-J.; Alper, H. J. Org. Chem. 1999, 64, 9646.
48. (j) Xiao, W.-J.; Vasapollo, G.; Alper, H. J. Org. Chem. 2000, 65, 4138.
49. (k) Xiao, W.-J.; Alper, H. J. Org. Chem. 2001, 66, 6229.
50. (l) Xiao, W.-J.; Alper, H. J. Org. Chem. 2005, 70, 1802.
51. (m) Cao, H.; Xiao, W.-J.; Alper, H. Adv. Synth. Catal. 2006, 348, 1807.
52. For the rhodium- or platinum-catalyzed thiocarbonylation, see: (n) Ogawa, A.; Kawakami, J; Mihara, M.; Ikeda, T.; Sonoda, N.; Hirao, T. J. Am. Chem. Soc. 1997, 119, 12380.
53. (o) Ogawa, A.; Kuniyasu, H.; Sonoda, N.; Hirao, T. J. Org. Chem. 1997, 62, 8361.
54. (p) Ogawa, A.; Obayashi, R.; Ine, H.; Tsuboi, Y.; Sonoda, N.; Hirao, T. J. Org. Chem. 1998, 63, 881.
55. (q) Kawakami, J.; Takeba, M.; Kamiya, I.; Sonoda, N.; Ogawa, A. Tetrahedron 2003, 59, 6559.
56. (r) Kawakami, J.; Mihara, M.; Kamiya, I.; Takeba, M.; Ogawa, A.; Sonoda, N. Tetrahedron 2003, 59, 3521.
57. (a) Davis, J. H. Chem. Lett. 2004, 33, 1072.
58. Task-specific ionic liquids, (b) Xue, H.; Verma, R.; Shreeve, J. M. Review of ionic liquids with fluorine-containing anions. J. Fluorine Chem. 2006, 127, 159.
59. (c) Shi, F.; Gu, Y.; Zhang, Y.; Deng, Y. Development of ionic liquids as green reaction media and catalysts. Catal. Surveys Asia 2004, 8, 179.
60. (d) Wasserscheid, P.; Welton, T. Ionic Liquid in Synthesis; Wiley-VCH &CoKGaA: Germay, 2002.
61. (a) Welton, T. Chem. Rev 1999, 99, 2071.
62. (b) Earle, M. J.; Seddon, K. R. Pure Appl. Chem. 2000, 72, 1391.
63. (c) Sheldon, R. A. Chem. Commun. (Cambridge) 2001, 2399.
64. (d) Wilkes, J. S. Green Chem. 2002, 4, 73.
65. (e) Dupont, J.; De Souza, R. F.; Suarez, P. A. Z. Chem. Rev. 2002, 102, 3667.
66. (a) Mizushima, E.; Hayashi, T.; Tanaka, M. Green Chem. 2001, 3, 76.
67. (b) Calo, V.; Giannoccaro, P.; Nacci, A.; Monopoli, A. J. Organomet. Chem. 2002, 645, 152.
68. (c) Li, Y.; Alper, H.; Yu, Z. K. Org. Lett. 2006, 8, 5199.
69. (d) Ye, F.; Alper, H. Adv. Synth. Catal. 2006, 348, 1855.
70. (e) Calo, V.; Nacci, A.; Monopoli, A. Eur. J. Org. Chem. 2006, 3791.
71. (f) Zhao, X.; Alper, H.; Yu, Z. J. Org. Chem. 2006, 71, 3988.
72. (g) Li, Y.; Yu, Z.; Alper, H. Org. Lett. 2007, 9, 1647.
73. (h) Ye, F.; Alper, H. J. Org. Chem. 2007, 72, 3219.
74. (i) Fukuyama, T.; Inouye, T.; Ryu, I. J. Organomet. Chem. 2007, 69, 2-685.
75. (j) Cao, H.; Alper, H. J. Org. Chem. 2007, 72, 8562.
76. (a) For a recent example, see: Mo, J.; Xu, L.; Ruan, J.; Shifang, S.; Xiao, J. Chem. Commun. 2006, 3591.
77. (b) For a comprehensive review, see: Wasserscheid, P.; Welton, T. Ionic Liquids in Synthesis Wiley-VCH: Weinheim, 2003.
78. (a) McNulty, J.; Capretta, A.; Wilson, J.; Dyck, J.; Adjabeng, G.; Robertson, A. J. J. Chem. Soc., Chem. Commun. 2002, 1986.
79. (b) Gerritsma, D. A.; Robertson, A. J.; McNulty, J.; Capretta, A. Tetrahedron Lett. 2004, 45, 7629.
80. (c) McNulty, J.; Capretta, A.; Cheekoori, S.; Clyburne, J. A. C.; Robertson, A. J. Chemica Oggi 2004, 22, 13.
81. (d) McNulty, J.; Cheekoori, S.; Nair, J. J.; Larichev, V.; Capretta, A.; Robertson, A. J. Tetrahedron Lett. 2005, 46, 3641.
82. (e) McNulty, J.; Nair, J. J.; Cheekoori, S.; Larichev, V.; Capretta, A.; Robertson, A. J. Chem. - Eur. J. 2006, 12, 9314.
83. (f) McNulty, J.; Cheekoori, S.; Bender, T. P.; Coggan, J. A. Eur. J. Org. Chem. 2007, 9, 1423.
84. (g) McNulty, J.; Nair, J. J.; Robertson, A. J. Org. Lett. 2007, 9, 4575.
85. (a) Bradaric, C. J.; Downard, A.; Kennedy, C.; Robertson, A. J.; Zhou, Y. Green Chem. 2003, 5, 143.
86. (b) Kim, Y. J.; Varma, R. S. J. Org. Chem. 2005, 70, 7882.
87. (a) Tsuji, J. In Palladium Reagents and Catalysts; Wiley: Chichester, UK, 2004; p 265.
88. (b) Skoda-Foldes, R.; Kollar, L. Curr. Org. Chem. 2002, 6, 1097.
89. (c) Mori, M. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002; Vol. 2, p 2663.
90. (d) Luh, T. Y.; Leung, M.; Wong, K. T. Chem. Rev. 2000, 100, 3187.
91. (e) Beller, M. Applied Homogeneous Catalysis with Organometallic Compounds, 2nd ed.; Cornils, B., Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, Germany, 2002; Vol. 1, p 145.
92. (f) Beller, M.; Cornils, B.; Frohning, C. D.; Kohlpaintner, C. W. J. Mol. Catal. 1995, 104, 17.
93. (g) Trost, B. M. Science 1991, 25, 4-1471.
94. (h) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259.
95. (i) Trost, B. M. Acc. Chem. Res. 2002, 35, 695.
96. (j) McNulty, J.; Nair, J. J.; Robertson, A. J. Org. Lett. 2007, 9, 4575.
97. (a) Sawada, N.; Itoh, T.; Yasuda, N. Tetrahedron Lett. 2006, 47 (37), 6595.
98. (b) J. Chem. Res. Synopses 2000, 8, 372.
99. (c) You, J.-Z.; Chen, Z.-C.; Synthesis 1992, 521.
100. (d) Cardellicchio, C.; Fiandanese, V.; Marchese, G.; Ronzini, L. Tetrahedron Lett. 1985, 26, 3595.
101. (e) Osuka, A.; Ohmasa, N.; Uno, Y.; Suzuki, H. Synthesis 1983, 68.