Direct conversion of carbon-hydrogen into carbon-carbon bonds by first-row transition-metal catalysis

Synthesis

Volumn , Issue 24, 2009, Pages 4087-4109

  Kulkarni, Amol A ^a   Daugulis, Olafs ^a  

^a University of Houston   (United States)

Author keywords

C H activation; Cobalt; Copper; Iron; Manganese; Nickel

Indexed keywords

C-H ACTIVATION; CARBON-CARBON BOND; CARBON-HYDROGEN BOND; DIRECT CONVERSION; EARTH'S CRUST; FUNCTIONALIZATION REACTIONS; METAL CATALYSIS;

ACTIVATION ANALYSIS; CATALYSIS; COBALT; COPPER; HYDROGEN; MANGANESE; NICKEL; STRUCTURAL GEOLOGY;

HYDROGEN BONDS;

ALDEHYDE; AZOBENZENE; CARBON; COBALT; COPPER; HYDANTOIN DERIVATIVE; HYDROGEN; INDOLE DERIVATIVE; IRON; MANGANESE; NAPHTHALENE; NICKEL; PYRIDINE;

ARYLATION; CARBON BOND; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL INTERACTION; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONFORMATIONAL TRANSITION; CROSS COUPLING REACTION; CYCLIZATION; ELECTRON TRANSPORT; HYDROGEN BOND; METAL METABOLISM; REVIEW; SYNTHESIS;

EID: 77249154012     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1217131     Document Type: Review

References (112)

1. (a) Barton, D. H. R. Tetrahedron 1998, 54, 5805.
2. (b) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879
3. (c) Dyker, G. Angew. Chem. Int. Ed. 1999, 38, 1699.
4. (d) Lewis, J. C.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2008, 41, 1013.
5. (e) Campeau, L.-C.; Fagnou, K. Chem. Commun. 2006, 1253.
6. (f) Ackermann, L. Synlett 2007, 50
7. (g) Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem. Int. Ed. 2009, 48, 5094.
8. (h) Seregin, I. V.; Gevorgyan, V. Chem. Soc. Rev. 2007, 36, 1173.
9. (i) Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911.
10. (a) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
11. (b) Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826.
12. (c) Davies, H. M. L.; Beckwith, R. E. J. Chem. Rev. 2003, 103, 2861.
13. (d) Dick, A. R.; Sanford, M. S. Tetrahedron 2006, 62, 2439.
14. (e) Díaz-Requejo, M. M.; Pérez, P. J. Chem. Rev. 2008, 108, 3379.
15. (f) Daugulis, O.; Do, H.-Q.; Shabashov, D. Acc. Chem. Res. 2009, 42, 1074.
16. (a) Enghag, P. Encyclopedia of the elements; Wiley: Weinheim, 2004.
17. (b) Cahiez, G.; Duplais, C.; Buendia, J. Chem. Rev. 2009, 109, 1434.
18. (c) Concellon, J. M.; Rodriguez-Solla, H.; del Amo, V. Chem. Eur. J. 2008, 14, 10184.
19. (d) McGarrigle, E. M.; Gilheany, D. G. Chem. Rev. 2005, 105, 1563.
20. Bennett, R. L.; Bruce, M. I.; Goodall, B. L.; Iqbal, M. Z.; Stone, F. G. A. J. Chem. Soc., Dalton Trans. 1972, 1787.
21. (a) Bruce, M. I.; Iqbal, M. Z.; Stone, F. G. A. J. Chem. Soc., A 1970, 3204.
22. (b) Bruce, M. I.; Goodall, B. L.; Stone, F. G. A. J. Chem. Soc., Chem. Commun. 1973, 558.
23. Gommans, L. H. P.; Main, L.; Nicholson, B. K. J. Chem. Soc., Chem. Commun. 1986, 12.
24. Liebeskind, L. S.; Gasdaska, J. R.; McCallum, J. S.; Tremont, S. J. J. Org. Chem. 1989, 54, 669
25. Kuninobu, Y.; Nishina, Y.; Takeuchi, T.; Takai, K. Angew. Chem. Int. Ed. 2007, 46, 6518.
26. Kuninobu, Y.; Kikuchi, K.; Takai, K. Chem. Lett. 2008, 37, 740.
27. Kuninobu, Y.; Kawata, A.; Nishi, M.; Takata, H.; Takai, K. Chem. Commun. 2008, 47, 6360.
28. (a) Weber K. A.; Achenbach L. A.; Coates, J. D. Nat Rev. Microbiol. 2006, 4, 752.
29. (b) Karan, E. F.; Bren, K. L. Chemtracts 2001, 14, 709.
30. (c) Castellani, R. J.; Moreira, P. I.; Liu, G.; Dobson, J.; Perry, G.; Smith, M. A.; Zhu, X. Neurochem. Res. 2007, 32, 1640.
31. (d) Bolm, C.; Legros, J.; Le Paih, J.; Zani, L. Chem. Rev. 2004, 104, 6217.
32. (e) Sherry, B. D.; Fürstner, A. Acc. Chem. Res. 2008, 41, 1500.
33. (f) Bauer, E. B. Curr. Org. Chem. 2008, 12, 134
34. (g) Gibson, V. C.; Redshaw, C.; Solan, G. A. Chem. Rev. 2007, 107, 1745.
35. Ittel, S. D.; Tolman, C. A.; English, A. D.; Jesson, J. P. J. Am. Chem. Soc. 1978, 100, 7577.
36. Jones, W. D.; Foster, G. P.; Putinas, J. M. J. Am. Chem. Soc. 1987, 109, 5047
37. Klein, H.-F.; Camadanli, S.; Beck, R.; Leukel, D.; Flörke, U. Angew. Chem. Int. Ed. 2005, 44, 975.
38. Li, P.; Zhang, Y.; Wang, L. Chem. Eur. J. 2009, 15, 2045.
39. Volla, C. M. R.; Vogel, P. Org. Lett. 2009, 11, 1701
40. Wen, J.; Zhang, J.; Chen, S.-Y.; Li, J.; Yu, X.-Q. Angew. Chem. Int. Ed. 2008, 47, 8897.
41. Norinder, J.; Matsumoto, A.; Yoshikai, N.; Nakamura, E. J. Am. Chem. Soc. 2008, 130, 5858
42. Yoshikai, N.; Matsumoto, A.; Norinder, J.; Nakamura, E. Angew. Chem. Int. Ed. 2009, 48, 2925.
43. (a) Li, C.-J. Acc. Chem. Res. 2002, 35, 533.
44. (b) Zhang, Y.; Li, C.-J. Eur. J. Org. Chem. 2007, 4654.
45. Li, Z.; Cao, L.; Li, C.-J. Angew. Chem. Int. Ed. 2007, 46, 6505
46. Li, Z.; Yu, R.; Li, H. Angew. Chem. Int. Ed. 2008, 47, 7497
47. Li, Y.-Z.; Li, B.-J.; Lu, X.-Y.; Lin, S.; Shi, Z.-J. Angew. Chem. Int. Ed. 2009, 48, 3817.
48. (a) Hess, W.; Treutwein, J.; Hilt, G. Synthesis 2008, 3537.
49. (b) Gosmini, C.; Begouin, J.-M.; Moncomble, A. Chem. Commun. 2008, 3221.
50. (c) Bianchini, C.; Giambastiani, G.; Rios, I. G.; Mantovani, G.; Meli, A.; Segarra, A. M. Coord. Chem. Rev. 2006, 250, 1391.
51. (d) Gibson, S. E.; Mainolfi, N. Angew. Chem. Int. Ed. 2005, 44, 3022.
52. Murahashi, S. J. Am. Chem. Soc. 1955, 77, 6403.
53. Murahashi, S.; Horiie, S. J. Am. Chem. Soc. 1956, 78, 4816.
54. Klein, H.-F.; Helwig, M.; Koch, U.; Flörke, U.; Haupt, H.-J. Z. Naturforsch. B: Chem. Sci. 1993, 48, 778.
55. Yu, F.; Li, X.; Sun, H. Z Anorg. Allg. Chem. 2006, 632, 501.
56. Beck, R.; Sun, H.; Li, X.; Klein, H.-F. Z Anorg. Allg. Chem. 2009, 635, 99.
57. (a) Heck, R. F. J. Am. Chem. Soc. 1968, 90, 313.
58. (b) Bruce, M. I.; Goodall, B. L.; Stone, F. G. A. J. Chem. Soc., Dalton Trans. 1975, 1651.
59. (c) Avilés, T.; Dinis, A.; Calhorda, M. J.; Pinto, P.; Félix, V.; Drew, M. G. B. J. Organomet. Chem. 2001, 625, 186.
60. (a) Lenges, C. P.; Brookhart, M. J. Am. Chem. Soc. 1997, 119, 3165.
61. (b) Marder, T. B.; Roe, C. D.; Milstein, D. Organometallics 1988, 7, 1451.
62. Lenges, C. P.; White, P. S.; Brookhart, M. J. Am. Chem. Soc. 1998, 120, 6965.
63. Beck, R.; Flörke, U.; Klein, H.-F. Inorg. Chem. 2009, 48, 1416.
64. Llerena, D.; Aubert, C.; Malacria, M. Tetrahedron Lett. 1996, 37, 7353.
65. Dolaine, R.; Gleason, J. L. Org. Lett. 2000, 2, 1753.
66. Ajamian, A.; Gleason, J. L. Org. Lett. 2001, 3, 4161.
67. Ajamian, A.; Gleason, J. L. Org. Lett. 2003, 5, 2409.
68. Li, L.; Jones, W. D. J. Am. Chem. Soc. 2007, 129, 10707.
69. Bolig, A. G.; Brookhart, M. J. Am. Chem. Soc. 2007, 129, 14544.
70. (a) Reymond, S.; Cossy, J. Chem. Rev. 2008, 108, 5359.
71. Ma, D.; Cai, Q. Acc. Chem. Res. 2008, 41, 1450.
72. Falciola, C. A.; Alexakis, A. Eur. J. Org. Chem. 2008, 22, 3765.
73. (d) Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054.
74. (e) Meldal, M.; Tornoe, C. W. Chem. Rev. 2008, 108, 2952.
75. (f) Yamada, K.-i.; Tomioka, K. Chem. Rev. 2008, 108, 2874.
76. (g) Stanley, L. M.; Sibi, M. P. Chem. Rev. 2008, 108, 2887.
77. Steinkopf, W.; Leitsmann, R.; Hofmann, K. H. Liebigs Ann. Chem. 1941, 546, 180.
78. Sease, J. W.; Zechmeister, L. J. Am. Chem. Soc. 1947, 69, 270.
79. Forrest, J. J. Chem. Soc. 1960, 574.
80. (a) Björklund, C.; Nilsson, M. Acta Chem. Scand. 1968, 22, 2338.
81. (b) Björklund, C.; Nilsson, M. Acta Chem. Scand. 1968, 22, 2581.
82. (c) Björklund, C.; Nilsson, M.; Wennerström, O. Acta Chem. Scand. 1970, 24, 3599.
83. Niu, M.; Yin, Z.; Fu, H.; Jiang, Y.; Zhao, Y. J. Org. Chem. 2008, 73, 3961.
84. Wang, M.; Li, P.; Wang, L. Eur. J. Org. Chem. 2008, 2255.
85. Phipps, R. J.; Grimster, N. P.; Gaunt, M. J. J. Am. Chem. Soc. 2008, 130, 8172.
86. Phipps, R. J.; Gaunt, M. J. Science 2009, 323, 1593.
87. (a) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174.
88. (b) Do, H.-Q.; Daugulis, O. J. Am. Chem. Soc. 2007, 129, 12404.
89. (c) Yoshizumi, T.; Tsurugi, H.; Satoh, T.; Miura, M. Tetrahedron Lett. 2008, 49, 1598.
90. (d) Besselièvre, F.; Piguel, S.; Mahuteau-Betzer, F.; Grierson, D. S. Org. Lett. 2008, 10, 4029.
91. (a) Do, H.-Q.; Daugulis, O. J. Am. Chem. Soc. 2008, 130, 1128.
92. (b) Matsubara, Y.; Kimura, A.; Yamaguchi, Y.; Yoshida, Z.-i. Org. Lett. 2008, 10, 5541.
93. Do, H.-Q.; Khan, R. M. K.; Daugulis, O. J. Am. Chem. Soc. 2008, 130, 15185.
94. Ban, I.; Sudo, T.; Taniguchi, T.; Itami, K. Org. Lett. 2008, 10, 3607.
95. Chen, X.; Dobereiner, G.; Hao, X.-S.; Giri, R.; Maugel, N.; Yu, J.-Q. Tetrahedron 2009, 65, 3085.
96. (a) Ackermann, L.; Potukuchi, H. K.; Landsberg, D.; Vicente, R. Org. Lett. 2008, 10, 3081.
97. (b) Yotphan, S.; Bergman, R. G.; Ellman, J. A. Org. Lett. 2009, 11, 151
98. (a) Montgomery, J. Angew. Chem. Int. Ed. 2004, 43, 3890.
99. (b) Ng, S.-S.; Ho, C.-Y.; Schleicher, K. D.; Jamison, T. F. Pure Appl. Chem. 2008, 80, 929.
100. (c) Terao, J.; Kambe, N. Acc. Chem. Res. 2008, 41, 1545.
101. (d) Denmark, S. E.; Butler, C. R. Chem. Commun. 2009, 20.
102. (e) Netherton, M. R.; Fu, G. C. Adv. Synth. Catal. 2004, 346, 1525.
103. (f) Jacobsen, E. N.; Breinbauer, R. Science 2000, 287, 437.
104. Kleiman, J. P.; Dubeck, M. J. Am. Chem. Soc. 1963, 85, 1544
105. (a) Kanyiva, K. S.; Nakao, Y.; Hiyama, T. Angew. Chem. Int. Ed. 2007, 46, 8872.
106. (b) Nakao, Y.; Kashihara, N.; Kanyiva, K. S.; Hiyama, T. J. Am. Chem. Soc. 2008, 130, 16170.
107. (c) Nakao, Y.; Kanyiva, K. S.; Hiyama, T. J. Am. Chem. Soc. 2008, 130, 2448.
108. Canivet, J.; Yamaguchi, J.; Ban, I.; Itami, K. Org. Lett. 2009, 11,1733.
109. Hachiya, H.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2009, 11, 1737.
110. Kobayashi, O.; Uraguchi, D.; Yamakawa, T. Org. Lett. 2009, 11, 2679.
111. Shirakura, M.; Suginome, M. J. Am. Chem. Soc. 2008, 130, 5410.
112. Yin, W.; He, C.; Chen, M.; Zhang, H.; Lei, A. Org. Lett. 2009, 11, 709.