Investigation of an efficient palladium-catalyzed C(sp)-C(sp) cross-coupling reaction using phosphine-olefin ligand: Application and mechanistic aspects

Journal of the American Chemical Society

Volumn 130, Issue 44, 2008, Pages 14713-14720

  Shi, Wei ^a   Luo, Yingdong ^a   Luo, Xiancai ^a   Chao, Lei ^a   Zhang, Heng ^a   Wang, Jian ^b   Lei, Aiwen ^a  

^a WUHAN UNIVERSITY   (China)

^b Mettler Toledo AutoChem   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; COPPER; HYDROCARBONS; LIGANDS; OLEFINS; PALLADIUM; PHOSPHORUS COMPOUNDS; PORT TERMINALS; REACTION RATES; SEMICONDUCTING INDIUM GALLIUM ARSENIDE;

CATALYTIC CYCLES; CONTROL EXPERIMENTS; COPPER SALTS; CROSS COUPLINGS; ELECTROPHILES; EXCELLENT YIELDS; FIRST ORDERS; HIGH SELECTIVITIES; KINETIC EVIDENCES; KINETIC STUDIES; MECHANISTIC ASPECTS; NEW PROTOCOLS; OLEFIN LIGANDS; REDUCTIVE ELIMINATIONS; SIDE REACTIONS; TERMINAL ALKYNES;

RATE CONSTANTS;

ALKENE; ALKYNE; COPPER; PALLADIUM; PHOSPHINE;

ARTICLE; CATALYSIS; CROSS COUPLING REACTION;

ALKYNES; BENZENE DERIVATIVES; CATALYSIS; CHEMICAL PROCESSES; KINETICS; PALLADIUM; PHOSPHINES; SPECTROPHOTOMETRY, INFRARED;

EID: 55549097483     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8049436     Document Type: Article

References (85)

1. Haley, M. M. Pure Appl. Chem. 2008, 80, 519-532.
2. Haley, M. M., Tykwinski, R. R., Eds.; Carbon-Rich Compounds: From Molecules to Materials; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2006.
3. Marsden, J. A.; Haley, M. M. J. Org. Chem. 2005, 70, 10213-10226.
4. Eisler, S.; Slepkov, A. D.; Elliott, E.; Luu, T.; McDonald, R.; Hegmann, F. A.; Tykwinski, R. R. J. Am. Chem. Soc. 2005, 127, 2666-2676.
5. Diederich, F., Stang, P. J., Tykwinski, R. R., Eds. Acetylene Chemistry: Chemistry, Biology and Material Science; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2005.
6. Nielsen, M. B.; Diederich, F. Chem. Rec. 2002, 2, 189-198.
7. Diederich, F. Chem. Commun. 2001, 219-227.
8. Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem., Int. Ed. 2000, 39, 2632-2657.
9. Zhou, Y.-Z.; Ma, H.-Y.; Chen, H.; Qiao, L.; Yao, Y.; Cao, J.-Q.; Pei, Y.-H. Chem. Pharm. Bull. 2006, 54, 1455-1456.
10. Kanokmedhakul, S.; Kanokmedhakul, K.; Kantikeaw, I.; Phonkerd, N. J. Nat. Prod. 2006, 69, 68-72.
11. Nakai, Y.; Sakakibara, I.; Hirakura, K.; Terabayashi, S.; Takeda, S. Chem. Pharm. Bull. 2005, 53, 1580-1581.
12. Stavri, M.; Mathew, K. T.; Gibson, T.; Williamson, R. T.; Gibbons, S. J. Nat. Prod. 2004, 67, 892-894.
13. Lerch, M. L.; Harper, M. K.; Faulkner, D. J. J. Nat. Prod. 2003, 66, 667-670.
14. de Jesus, R. P.; Faulkner, D. J. J. Nat. Prod. 2003, 66, 671-674.
15. Ladika, M.; Fisk, T. E.; Wu, W. W.; Jons, S. D. J. Am. Chem. Soc. 1994, 116, 12093-12094.
16. Matsunaga, H.; Katano, M.; Yamamoto, H.; Fujito, H.; Mori, M.; Takata, K. Chem. Pharm. Bull. 1990, 38, 3480-3482.
17. Kim, Y. S.; Jin, S. H.; Kim, S. I.; Hahn, D. R. Arch. Pharmacol. Res. 1989, 12, 207-213.
18. Lv, X.; Mao, J.; Liu, Y.; Huang, Y.; Ma, Y.; Yu, A.; Yin, S.; Chen, Y. Macromolecules 2008, 41, 501-503.
19. Poon, S.-Y.; Wong, W.-Y.; Cheah, K.-W.; Shi, J.-X. Chem.-Eur. J. 2006, 12, 2550-2563.
20. Egbe, D. A. M.; Birckner, E.; Klemm, E. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 2670-2679.
21. Hoger, S.; Meckenstock, A.-D. Chem.-Eur. J. 1999, 5, 1686-1691.
22. Diederich, F.; Stang, P. J. Metal-catalyzed cross-coupling reactions; Wiley-VCH: Weinheim/New York, 1998.
23. Shun, A. L. K. S.; Tykwinski, R. R. Angew. Chem., Int. Ed. 2006, 45, 1034-1057.
24. Zhang, C.; Chen, C.-F. J. Org. Chem. 2007, 72, 9339-9341.
25. Marsden, J. A.; Miller, J. J.; Haley, M. M. Angew. Chem., Int. Ed. 2004, 43, 1694-1697.
26. Marsden, J. A.; Haley, M. M. Cross-coupling reactions to sp carbon atoms; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2004; Vol. 1.
27. Kim, S.; Kim, S.; Lee, T.; Ko, H.; Kim, D. Org. Lett. 2004, 6, 3601-3604.
28. Gung, B. W.; Kumi, G. J. Org. Chem. 2004, 69, 3488-3492.
29. Bellina, F.; Carpita, A.; Mannocci, L.; Rossi, R. Eur. J. Org. Chem. 2004, 2610-2619.
30. Reber, S.; Knopfel, T. F.; Carreira, E. M. Tetrahedron 2003, 59, 6813-6817.
31. Youngblood, W. J.; Gryko, D. T.; Lammi, R. K.; Bocian, D. F.; Holten, D.; Lindsey, J. S. J. Org. Chem. 2002, 67, 2111-2117.
32. Marino, J. P.; Nguyen, H. N. J. Org. Chem. 2002, 67, 6841-6844.
33. Ohkita, M.; Ando, K.; Suzuki, T.; Tsuji, T. J. Org. Chem. 2000, 65, 4385-4390.
34. Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.-i.; Mori, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780-1787.
35. Nguyen, P.; Yuan, Z.; Agocs, L.; Lesley, G.; Marder, T. B. Inorg. Chim. Acta 1994, 220, 289-296.
36. Nye, S. A.; Potts, K. T. Synthesis 1988, 375-377.
37. Constantino, M. G.; Donate, P. M.; Petragnani, N. J. Org. Chem. 1986, 51, 387-390.
38. Chodkiewicz, W. Ann. Chim. 1957, 2, 819-869.
39. Negishi, E.-I.; Anastasia, L. Chem. Rev. 2003, 103, 1979-2017.
40. Yadav, J. S.; Reddy, B. V. S.; Reddy, K. B.; Gayathri, K. U.; Prasad, A. R. Tetrahedron Lett. 2003, 44, 6493-6496.
41. Li, J.; Jiang, H. Chem. Commun. 1999, 2369-2370.
42. Hoeger, S.; Meckenstock, A.-D.; Pellen, H. J. Org. Chem. 1997, 62, 4556-4557.
43. Cameron, M. D.; Bennett, G. E. J. Org. Chem. 1957, 22, 557-558.
44. Jiang, H.-F.; Wang, A. Z. Synthesis 2007, 1649-1654.
45. Lopez, S.; Fernandez-Trillo, F.; Midon, P.; Castedo, L.; Saa, C. J. Org. Chem. 2006, 71, 2802-2810.
46. Gung, B. W.; Dickson, H. Org. Lett. 2002, 4, 2517-2519.
47. Montierth, J. M.; DeMario, D. R.; Kurth, M. J.; Schore, N. E. Tetrahedron 1998, 54, 11741-11748.
48. Chodkiewicz, W.; Cadiot, P. Compt. Rend. 1955, 241, 1055-1057.
49. Alami, M.; Ferri, F. Tetrahedron Lett. 1996, 37, 2763-2766.
50. Dyker, G., Ed. Handbook of C-H Transformations: Applications in Organic Synthesis; Wiley-VCH: Weinheim, 2005; Vol. 2.
51. Batsanov, A. S.; Collings, J. C.; Fairlamb, I. J. S.; Holland, J. P.; Howard, J. A. K.; Lin, Z.; Marder, T. B.; Parsons, A. C.; Ward, R. M.; Zhu, J. J. Org. Chem. 2005, 70, 703-706.
52. Negishi, E.-i.; Qian, M.; Zeng, F.; Anastasia, L.; Babinski, D. Org. Lett. 2003, 5, 1597-1600.
53. Qian, M.; Negishi, E. Org. Process Res. Dev. 2003, 7, 412-417.
54. Negishi, E.-i.; de Meijere, A. Handbook of organopalladium chemistry for organic synthesis; Wiley-Interscience: New York, 2002.
55. Negishi, E.; Okukado, N.; Lovich, S. F.; Luo, F. T. J. Org. Chem. 1984, 49, 2629-2632.
56. Shi Shun, A. L. K.; Chernick, E. T.; Eisler, S.; Tykwinski, R. R. J. Org. Chem. 2003, 68, 1339-1347.
57. Luu, T.; Morisaki, Y.; Cunningham, N.; Tykwinski, R. R. J. Org. Chem. 2007, 72, 9622-9629.
58. Eisler, S.; Tykwinski, R. R. J. Am. Chem. Soc. 2000, 122, 10736-10737.
59. Wityak, J.; Chan, J. B. Synth. Commun. 1991, 21, 977-979.
60. Crabtree, R. H. The organometallic chemistry of the transition metals, 4th ed.; Wiley-Interscience: Hoboken, NJ, 2005.
61. Miyaura, N. Cross-Coupling Reactions. A Practical Guide; Topics in Current Chemistry 219; Springer: Berlin, 2002; p 2002.
62. Tsuji, J. Transition metal reagents and catalysts: innovations in organic synthesis; Wiley: Chichester/New York, 2000.
63. Johnson, J. B.; Rovis, T. Angew. Chem., Int. Ed. 2008, 47, 840-871.
64. Fairlamb, I. J. S.; Kapdi, A. R.; Lee, A. F. Org. Lett. 2004, 6, 4435-4438.
65. Fairlamb, I. J. S.; Kapdi, A. R.; Lee, A. F.; McGlacken, G. P.; Weissburger, F.; de Vries, A. H. M.; Schmieder-van de Vondervoort, L. Chem.-Eur. J. 2006, 12, 8750-8761.
66. Fairlamb, I. J. S.; Lee, A. F. Organometallics 2007, 26, 4087-4089.
67. Mace, Y.; Kapdi, A. R.; Fairlamb, I. J. S.; Jutand, A. Organometallics 2006, 25, 1795-1800.
68. Bercot, E. A.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 174-175.
69. Bercot, E. A.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 10248-10249.
70. Johnson, J. B.; Bercot, E. A.; Rowley, J. M.; Coates, G. W.; Rovis, T. J. Am. Chem. Soc. 2007, 129, 2718-2725.
71. Rogers, R. L.; Moore, J. L.; Rovis, T. Angew. Chem., Int. Ed. 2007, 46, 9301-9304.
72. Zhang, Y.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 15964-15965.
73. Wang, Z.-Q.; Feng, C.-G.; Xu, M.-H.; Lin, G.-Q. J. Am. Chem. Soc. 2007, 129, 5336-5337.
74. Shintani, R.; Duan, W.-L.; Nagano, T.; Okada, A.; Hayashi, T. Angew. Chem., Int. Ed. 2005, 44, 4611-4614.
75. Williams, D. B. G.; Shaw, M. L. Tetrahedron 2007, 63, 1624-1629.
76. Luo, X.; Zhang, H.; Duan, H.; Liu, Q.; Zhu, L.; Zhang, T.; Lei, A. Org. Lett. 2007, 9, 4571-4574.
77. Metay, E.; Hu, Q.; Negishi, E.-I. Org. Lett. 2006, 8, 5773-5776.
78. Blackmond, D. G. Angew. Chem., Int. Ed. 2005, 44, 4302-4320.
79. Blackmond, D. G.; Hodnett, N. S.; Lloyd-Jones, G. C. J. Am. Chem. Soc. 2006, 128, 7450-7451.
80. Mathew, J. S.; Klussmann, M.; Iwamura, H.; Valera, F.; Futran, A.; Emanuelsson, E. A. C.; Blackmond, D. G. J. Org. Chem. 2006, 71, 4711-4722.
81. Izawa, Y.; Shimizu, I.; Yamamoto, A. Bull. Chem. Soc. Jpn. 2004, 77, 2033-2045.
82. 3 (vs Pd) and Pd was slower than that catalyzed by L1/Pd (see Figure 10). So the olefin part of L1 should have played a role in accelerating the reaction. Thus, we speculated that, in our system, 6-II as the reductive elimination precursor was more possible than an active tri-coordinated Pd complex.
83. Yamashita, M.; Hartwig, J. F. J. Am. Chem. Soc. 2004, 126, 5344-5345.
84. Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 4708-4709.
85. Moravskiy, A.; Stille, J. K. J. Am. Chem. Soc. 1981, 103, 4182-4186.