Synthetic and mechanistic studies of Pd-catalyzed C-H arylation with diaryliodonium salts: Evidence for a bimetallic high oxidation state Pd intermediate

Journal of the American Chemical Society

Volumn 131, Issue 31, 2009, Pages 11234-11241

  Deprez, Nicholas R ^a   Sanford, Melanie S ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2-PHENYLPYRIDINE; ARYL GROUP; ARYLATIONS; CATALYTIC INTERMEDIATES; CATALYTIC REACTIONS; DIARYLIODONIUM SALTS; ELECTRONIC INFLUENCE; HIGH OXIDATION STATE; HIGH YIELD; KINETIC ISOTOPE EFFECTS; KINETIC ORDER; MECHANISTIC STUDIES; OXAZOLIDINONES; PD SPECIES; RESTING STATE;

AROMATIC COMPOUNDS; CATALYSIS; CATALYTIC OXIDATION; INDUSTRIAL CHEMICALS; IODINE; ISOTOPES; OXIDATION; REACTION RATES; SALTS;

PALLADIUM;

2 PYRROLIDONE DERIVATIVE; CARBON; HYDROGEN; IODINE; ISOTOPE; LIGAND; OXAZOLIDINONE DERIVATIVE; PALLADIUM; PYRIDINE DERIVATIVE; QUINOLINE DERIVATIVE; REAGENT; SODIUM CHLORIDE;

ARTICLE; ARYLATION; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; MOLECULAR ELECTRONICS; OXIDATION; SYNTHESIS; TRANSPORT KINETICS;

CATALYSIS; ELECTRONS; HYDROCARBONS, AROMATIC; IONS; PALLADIUM; SALTS;

EID: 68249136644     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja904116k     Document Type: Article

References (102)

1. (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
2. (b) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1.
3. (c) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
4. (d) Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
5. (e) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
6. (f) Kotha, S.; Lahiri, K.; Kashinath, D. Tetrahedron 2002, 58, 9633.
7. (g) Denmark, S. E.; Sweis, R. F. Acc. Chem. Res. 2002, 35, 835.
8. (h) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
9. (i) Negishi, E.; Anastasia, L. Chem. Rev. 2003, 103, 1979.
10. For recent reviews that discuss C-H arylation, see: (a) Campeau, L. C.; Fagnou, K. Chem. Commun. 2006, 1253.
11. (b) Daugulis, O.; Zaitsev, V. G.; Shabashov, D.; Pham, Q. N.; Lazareva, A. Synlett 2006, 3382.
12. (c) Yu, J. Q.; Giri, R.; Chen, X. Org. Biomol. Chem. 2006, 4, 4041.
13. (d) Godula, K.; Sames, D. Science 2006, 312, 67.
14. (e) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174.
15. (f) Beccalli, E. M.; Broggini, G.; Martinelli, M.; Sottocornola, S. Chem. Rev. 2007, 107, 5318.
16. (g) Ackermann, L. Synlett 2007, 507.
17. (h) Fairlamb, I. J. S. Chem. Soc. Rev. 2007, 36, 1036.
18. (i) Campeau, L. C.; Fagnou, K. Chem. Soc. Rev. 2007, 36, 1058.
19. (j) Catellani, M.; Motti, E.; Della Ca, N. Acc. Chem. Res. 2008, 41, 1512.
20. (k) Kakiuchi, F.; Kochi, T. Synthesis 2008, 3013.
21. (l) Li, B. J.; Yand, S. D.; Shi, Z. J. Synlett 2008, 949.
22. (m) McGlacken, G. P.; Bateman, L. M. Chem. Soc. Rev. 2009, DOI: 10.1039/b805701j.
23. For examples of ligand-directed Ar-H oxidative coupling, see: (a) Hull, K. L.; Lanni, E. L.; Sanford, M. S. J. Am. Chem. Soc. 2006, 128, 14047.
24. (b) Xia, J. B.; You, S. L. Organometallics 2007, 26, 4869.
25. (c) Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2007, 129, 11904.
26. (d) Li, B. J.; Tian, S. L.; Fang, Z.; Shi, Z. J. Angew. Chem., Int. Ed. 2008, 47, 1115.
27. (e) Brasche, G.; García-Fortanet, J.; Buchwald, S. L. Org. Lett. 2008, 10, 2207.
28. II/IV mechanism, see ref 5a and: (a) Shabashov, D.; Daugulis, O. Org. Lett. 2005, 7, 3657.
29. (b) Zaitsev, V. G.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 13154.
30. (c) Reddy, B. V. S.; Reddy, L. R.; Corey, E. J. Org. Lett. 2006, 8, 3391.
31. (d) Giri, R.; Maugel, N.; Li, J. J.; Wang, D. H.; Breazzano, S. P.; Saunders, L. B.; Yu, J. Q. J. Am. Chem. Soc. 2007, 129, 3510.
32. (e) Chiong, H. A.; Pham, Q. N.; Daugulis, O. J. Am. Chem. Soc. 2007, 129, 9879.
33. (f) Thirunavukkarasu, V. S.; Parthasarathy, K.; Cheng, C. H. Angew. Chem., Int. Ed. 2008, 47, 9462.
34. (g) Yang, F.; Wu, Y.; Zhu, Z.; Zhang, J.; Li, Y. Tetrahedron 2008, 64, 6782.
35. (h) Yang, F.; Wu, Y.; Li, Y.; Wang, B.; Zhang, J. Tetrahedron 2009, 65, 914.
36. (a) Kalyani, D.; Deprez, N. R.; Desai, L. V.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 7330.
37. (b) Deprez, N. R.; Kalyani, D.; Sanford, M. S. J. Am. Chem. Soc. 2006, 128, 4972.
38. 2I]X in C-H arylation, see: (a) Daugulis, O.; Zaitsev, V. G. Angew. Chem., Int. Ed. 2005, 44, 4046.
39. (b) Phipps, R. J.; Grimster, N. P.; Gaunt, M. J. J. Am. Chem. Soc. 2008, 130, 8172.
40. (c) Phipps, R. J.; Gaunt, M. J. Science 2009, 323, 1593.
41. (a) Bayler, A.; Canty, A. J.; Ryan, J. H.; Skelton, B. W.; White, A. H. Inorg. Chem. Commun. 2000, 3, 575.
42. (b) Canty, A. J.; Rodemann, T. Inorg. Chem. Commun. 2003, 6, 1382.
43. (c) Canty, A. J.; Patel, J.; Rodemann, T.; Ryan, J. H.; Skelton, B. W.; White, A. H. Organometallics 2004, 23, 3466.
44. (d) Canty, A. J.; Rodemann, T.; Skelton, B. W.; White, A. H. Inorg. Chem. Commun. 2005, 8, 55.
45. (e) Canty, A. J.; Rodemann, T.; Skelton, B. W.; White, A. H. Organometallics 2006, 25, 3996.
46. (f) Chaudhuri, P. D.; Guo, R.; Malinakova, H. C. J. Organomet. Chem. 2007, 693, 567.
47. IV with an iodine(III) reagent, see: (a) Lagunas, M. C.; Gossage, R. A.; Spek, A. L.; van Koten, G. Organometallics 1998, 17, 731.
48. (b) Dick, A. R.; Kampf, J. W.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 12790.
49. (c) Whitfield, S. R.; Sanford, M. S. J. Am. Chem. Soc. 2007, 129, 15142.
50. (d) Racowski, J. M.; Dick, A. R.; Sanford, M. S. J. Am. Chem. Soc. 2009, ASAP article.
51. Kalyani, D.; Sanford, M. S. Org. Lett. 2005, 7, 4149.
52. 0 nanoparticles. For a review, see: Weck, M.; Jones, C. W. Inorg. Chem. 2007, 46, 1865.
53. Kraatz, H. B.; van der Boom, M. E.; Ben-David, Y.; Milstein, D. Isr. J. Chem 2001, 41, 163.
54. All of the order studies were conducted under conditions where [1] > ([4] + [Pd]). When [1] < ([4] + [Pd]), the kinetics become much more complex, and the order in [1] deviates from inverse third order (see Supporting Information p S16). This is expected based on the proposed mechanism, since under these conditions, the resting state of the oxidant is a mixture of 8 and 4.
55. -4.
56. (a) Boele, M. D. K.; van Strijdonck, G. P. F.; de Vries, A. H. M.; Kamer, P. C. J.; de Vries, J. G.; van Leeuwen, P. W. N. M. J. Am. Chem. Soc. 2002, 124, 1586.
57. (b) Zaitsev, V. G.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 4156.
58. (c) Giri, R.; Chen, X.; Yu, J. Q. Angew. Chem., Int. Ed. 2005, 44, 2112.
59. (d) Wang, D. H.; Hao, X. S.; Wu, D. F.; Yu, J. Q. Org. Lett. 2006, 8, 3387.
60. (e) Chen, X.; Goodhue, C. E.; Yu, J. Q. J. Am. Chem. Soc, 2006, 128, 12634.
61. (f) Chiong, H. A.; Pham, Q. N.; Daugulis, O. J. Am. Chem. Soc. 2007, 129, 9879.
62. (g) Xia, J. B.; You, S. L. Organometallics 2007, 26, 4869.
63. (h) Desai, L. V.; Stowers, K. J.; Sanford, M. S. J. Am. Chem. Soc. 2008, 130, 13285.
64. Ryabov, A. D. Inorg. Chem. 1987, 26, 1252.
65. (a) Weiss, R.; Seubert, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 891.
66. (b) Zhdankin, V. V.; Koposov, A. Y.; Yashin, N. V. Tetrahedron Lett. 2002, 43, 5735.
67. (c) Ochiai, M.; Suefuji, T.; Miyamoto, K.; Shiro, M. Chem. Commun. 2003, 1438.
68. (d) Suefuji, T.; Shiro, M.; Yamaguchi, K.; Ochiai, M. Heterocycles 2006, 67, 391.
69. A Job plot at 80°C also displayed a maximum at 0.5 and is available in the Supporting Information.
70. Blanda, M. T.; Horner, J. H.; Newcomb, M. J. Org. Chem. 1989, 54, 4626.
71. Job, A. Ann. Chem. 1928, 9, 113.
72. (a) Funasaki, N.; Ishikawa, S.; Neya, S. Bull. Chem. Soc. Jpn. 2002, 75, 719.
73. (b) Bisson, A. P.; Hunter, C. A.; Morales, J. C.; Young, K. Chem. Eur. J. 1998, 4, 845.
74. (c) Fielding, L. Tetrahedron 2000, 56, 6151.
75. Ansyln, E. K.; Dougherty, D. A. Modern Physical Organic Chemistry; University Science Books: Sausalito, CA, 2006; p 447.
76. For recent selected examples of intramolecular kinetic isotope effects in Pd-catalyzed ligand-directed C-H functionalization reactions, see refs 14b, d, e, and f as well as: (a) Cai, G.; Fu, Y.; Li, Y.; Wan, X.; Shi, Z. J. Am. Chem. Soc. 2007, 129, 7666.
77. (b) Shi, Z.; Li, B.; Wan, X.; Cheng, J.; Fang, Z.; Cao, B.; Qin, C.; Wang, Y. Angew. Chem., Int. Ed. 2007, 46, 5554.
78. (c) Li, J. J.; Giri, R.; Yu, J. Q. Tetrahedron 2008, 64, 6979.
79. (d) Kirchberg, S.; Vogler, T.; Studer, A. Synlett 2008, 2841.
80. Stille, J. K.; Lau, K. S. Y. Acc. Chem. Res. 1977, 10, 434.
81. (a) Thu, H. Y.; Yu, W. Y.; Che, C. M. J. Am. Chem. Soc. 2006, 128, 9048.
82. (b) Kim, M.; Taylor, T. J.; Gabbaï, F. P. J. Am. Chem. Soc. 2008, 130, 6332.
83. Cotton, F. A.; Koshevoy, I. O.; Lahuerta, P.; Murillo, C. A.; Sanau, M.; Ubeda, M. A.; Zhao, Q. J. Am. Chem. Soc. 2006, 128, 13674.
84. Cotton, F. A.; Gu, J.; Murillo, C. A.; Timmons, D. J. J. Am. Chem. Soc. 1998, 120, 13280.
85. Powers, D. C.; Ritter, T. Nat. Chem. 2009, 1, 302.
86. Baxter, L. A. M.; Heath, G. A.; Raptis, R. G.; Willis, A. C. J. Am. Chem. Soc. 1992, 114, 6944.
87. Dick, A. R.; Kampf, J. W.; Sanford, M. S. Organometallics 2005, 24, 482.
88. Canty, A. J.; Gardiner, M. G.; Jones, R. C.; Rodemann, T.; Sharma, M. J. Am. Chem. Soc. 2009, 131, 7236.
89. Our initial report on the mechanism of Pd-catalyzed C-H acetoxylation used benzylpyridines as substrates (ref 14h). However, recent studies have shown analogous order and KIE data with 2-phenylpyridine derivatives. Stowers, K. J.; Sanford, M. S. manuscript in preparation.
90. (a) Alexanian, E. J.; Lee, C.; Sorensen, E. J. J. Am. Chem. Soc. 2005, 127, 7690.
91. (b) Streuff, J.; Hövelmann, C. H.; Nieger, M.; Muñiz, K. J. Am. Chem. Soc. 2005, 127, 14586.
92. (c) Liu, G.; Stahl, S. S. J. Am. Chem. Soc. 2006, 128, 7179.
93. (d) Desai, L. V.; Sanford, M. S. Angew. Chem., Int. Ed. 2007, 46, 5737.
94. (e) Muñiz, K. J. Am. Chem. Soc. 2007, 129, 14542.
95. (f) Muñiz, K.; Hövelmann, C. H.; Streuff, J. J. Am. Chem. Soc. 2008, 130, 763.
96. Li, Y.; Song, D.; Dong, V. M. J. Am. Chem. Soc. 2008, 130, 2962.
97. (a) Tong, X.; Beller, M.; Tse, M. K. J. Am. Chem. Soc. 2007, 129, 4906.
98. (b) Welbes, L. L.; Lyons, T. W.; Cychosz, K. A.; Sanford, M. S. J. Am. Chem. Soc. 2007, 129, 5836.
99. (c) Liu, H.; Yu, J.; Wang, L.; Tong, X. Tetrahedron Lett. 2008, 49, 6924.
100. (d) Yin, G.; Liu, G. Angew. Chem., Int. Ed. 2008, 47, 5442.
101. (e) Lyons, T. W.; Sanford, M. S. Tetrahedron 2009, 65, 3211.
102. (f) Tsujihara, T.; Takenaka, K.; Onitsuka, K.; Hatanaka, M.; Sasai, H. J. Am. Chem. Soc. 2009, 131, 3452.