The redox-neutral approach to C-H functionalization

Chemistry - A European Journal

Volumn 19, Issue 40, 2013, Pages 13274-13287

  Peng, Bo ^a   Maulide, Nuno ^a  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

Author keywords

atom economy; C H activation; C H functionalization; hydride transfer; redox chemistry

Indexed keywords

ATOM ECONOMY; C-H ACTIVATION; C-H FUNCTIONALIZATION; HYDRIDE TRANSFERS; REDOX CHEMISTRY;

ACTIVATION ANALYSIS; FUNCTIONAL GROUPS;

HYDRIDES;

EID: 84884815030     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201301522     Document Type: Review

References (100)

1. G. Dyker, Handbook of C-H Transformations. Applications in Organic Synthesis, Wiley-VCH, Weinheim, 2005
2. J. A. Labinger, J. E. Bercaw, Nature 2002, 417, 507-514
3. K. Godula, D. Sames, Science 2006, 312, 67-72
4. T. Brückl, R. D. Baxter, Y. Ishihara, P. S. Baran, Acc. Chem. Res. 2012, 45, 826-839
5. S.-Y. Zhang, F.-M. Zhang, Y.-Q. Tu, Chem. Soc. Rev. 2011, 40, 1937-1949
6. T. Newhouse, P. S. Baran, Angew. Chem. 2011, 123, 3422-3435
7. Angew. Chem. Int. Ed. 2011, 50, 3362-3374.
8. Z. Ren, F. Mo, G. Dong, J. Am. Chem. Soc. 2012, 134, 16991-16994
9. E. M. Simmons, J. F. Hartwig, Nature 2012, 483, 70-73
10. C. J. Shaffer, D. Schröder, C. Gütz, A. Lützen, Angew. Chem. 2012, 124, 8221-8224
11. Angew. Chem. Int. Ed. 2012, 51, 8097-8100
12. M. A. Bigi, S. A. Reed, M. C. White, Nat. Chem. 2011, 3, 216-222
13. G. He, G. Chen, Angew. Chem. 2011, 123, 5298-5302
14. Angew. Chem. Int. Ed. 2011, 50, 5192-5196
15. R. Giri, N. Maugel, B. M. Foxman, J.-Q. Yu, Organometallics 2008, 27, 1667-1670
16. V. G. Zaitsev, D. Shabashov, O. Daugulis, J. Am. Chem. Soc. 2005, 127, 13154-13155
17. J. A. Johnson, N. Li, D. Sames, J. Am. Chem. Soc. 2002, 124, 6900-6903
18. C. G. Espino, J. D. Bois, Angew. Chem. 2001, 113, 618-620
19. Angew. Chem. Int. Ed. 2001, 40, 598-600
20. C. G. Espino, P. M. Wehn, J. Chow, J. D. Bois, J. Am. Chem. Soc. 2001, 123, 6935-6936.
21. A. W. Hofmann, Ber. Dtsch. Chem. Ges. 1883, 16, 558-560
22. A. W. Hofmann, Ber. Dtsch. Chem. Ges. 1885, 18, 5-23
23. E. J. Corey, W. R. Hertler, J. Am. Chem. Soc. 1960, 82, 1657-1668
24. M. E. Wolff, Chem. Rev. 1963, 63, 55-64
25. K. Chen, J. M. Richter, P. S. Baran, J. Am. Chem. Soc. 2008, 130, 7247-7249
26. A. F. Voica, A. Mendoza, W. R. Gutekunst, J. O. Fraga, P. S. Baran, Nat. Chem. 2012, 4, 629-635
27. Q. Michaudel, D. Thevenet, P. S. Baran, J. Am. Chem. Soc. 2012, 134, 2547-2550.
28. R. Breslow, S. Baldwin, T. Flechtner, P. Kalicky, S. Liu, W. Washburn, J. Am. Chem. Soc. 1973, 95, 3251-3262
29. Z. Čekoviõ, L. Dimitrijevic̈, G. Djokic̈, T. Srnic̈, Tetrahedron 1979, 35, 2021-2026.
30. S. J. Pastine, K. M. McQuaid, D. Sames, J. Am. Chem. Soc. 2005, 127, 12180-12181
31. K. M. McQuaid, D. Sames, J. Am. Chem. Soc. 2009, 131, 402-403; for an early Lewis acid mediated process, see
32. M. Noguchi, H. Yamada, T. Sunagawa, J. Chem. Soc. Perkin Trans. 1 1998, 3327-3329.
33. W. H. N. Nijhuis, W. Verboom, D. N. Reinhoudt, Synthesis 1987, 641-645
34. W. H. N. Nijhuis, W. Verboom, D. N. Reinhoudt, J. Am. Chem. Soc. 1987, 109, 3136-3138; the first example of such a process dates back more than a century ago, to 1895
35. J. Pinnow, Ber. Dtsch. Chem. Ges. 1895, 28, 3039; the term "tert-amino effect" was first used in 1972
36. O. Meth-Cohn, H. Suschitzky, Adv. Heterocycl. Chem. 1972, 14, 211-278; for other reviews, see
37. O. Meth-Cohn, Adv. Heterocycl. Chem. 1996, 65, 1-37
38. P. Mátyus, O. Éliás, P. Tapolcsányi, Á. Polonka-Bálint, B. Halász-Dajka, Synthesis 2006, 2625-2639.
39. S. C. Pan, Beilstein J. Org. Chem. 2012, 8, 1374-1384
40. M. Wang, ChemCatChem 2013, 5, 1291-1293
41. M. Tobisu, N. Chatani, Angew. Chem. 2006, 118, 1713-1715
42. Angew. Chem. Int. Ed. 2006, 45, 1683-1684.
43. S. Murarka, C. Zhang, M. D. Konieczynska, D. Seidel, Org. Lett. 2009, 11, 129-132.
44. K. M. McQuaid, J. Z. Long, D. Sames, Org. Lett. 2009, 11, 2972-2975.
45. 3-catalyzed 1,5-hydride-transfer/ring-closure reaction, see:, Y.-Y. Han, W.-Y. Han, X. Hou, X.-M. Zhang, W.-C. Yuan, Org. Lett. 2012, 14, 4054-4057.
46. K. Mori, T. Kawasaki, S. Sueoka, T. Akiyama, Org. Lett. 2010, 12, 1732-1735.
47. M. C. Haibach, I. Deb, C. K. De, D. Seidel, J. Am. Chem. Soc. 2011, 133, 2100-2103.
48. M. Alajarin, M. Marin-Luna, A. Vidal, Adv. Synth. Catal. 2011, 353, 557-562.
49. S. J. Pastine, D. Sames, Org. Lett. 2005, 7, 5429-5431.
50. R. B. Woodward, F. Sondheimer, Y. Mazur, J. Am. Chem. Soc. 1958, 80, 6693-6694.
51. W. Verboom, M. R. J. Hamzink, D. N. Reinhoudt, R. Visser, Tetrahedron Lett. 1984, 25, 4309-4312
52. D. N. Reinhoudt, G. W. Visser, W. Verboom, P. H. Benders, M. L. M. Pennings, J. Am. Chem. Soc. 1983, 105, 4775-4781
53. E. O. M. Orlemans, B. H. M. Lammerink, F. C. J. M. van Veggel, W. Verboom, S. Harkema, D. N. Reinhoudt, J. Org. Chem. 1988, 53, 2278-2287.
54. C. Zhang, S. Murarka, D. Seidel, J. Org. Chem. 2009, 74, 419-422
55. K. Mori, Y. Ohshima, K. Ehara, T. Akiyama, Chem. Lett. 2009, 38, 524-525.
56. S. V. Ryabukhin, A. S. Plaskon, D. M. Volochnyuk, A. N. Shivanyuk, A. A. Tolmachev, J. Org. Chem. 2007, 72, 7417-7419.
57. P. A. Vadola, D. Sames, J. Am. Chem. Soc. 2009, 131, 16525-16528.
58. I. Dias-Jurberg, Y. Odabachian, F. Gagosz, J. Am. Chem. Soc. 2010, 132, 3543-3552.
59. N. Morita, N. Krause, Org. Lett. 2004, 6, 4121-4123
60. N. Nishina, Y. Yamamoto, Angew. Chem. 2006, 118, 3392-3395
61. Angew. Chem. Int. Ed. 2006, 45, 3314-3317
62. Z. Zhang, C. Liu, R. E. Kinder, X. Han, H. Qian, R. A. Widenhoefer, J. Am. Chem. Soc. 2006, 128, 9066-9073
63. R. L. LaLonde, B. D. Sherry, E. J. Kang, F. D. Toste, J. Am. Chem. Soc. 2007, 129, 2452-2453.
64. B. Bolte, F. Gagosz, J. Am. Chem. Soc. 2011, 133, 7696-7699.
65. N. D. Shapiro, V. Rauniyar, G. L. Hamilton, J. Wu, F. D. Toste, Nature 2011, 470, 245-249.
66. D. Shikanai, H. Murase, T. Hata, H. Urabe, J. Am. Chem. Soc. 2009, 131, 3166-3167.
67. D. Chen, Z. Han, Y. He, J. Yu, L. Gong, Angew. Chem. 2012, 124, 12473-12476
68. Angew. Chem. Int. Ed. 2012, 51, 12307-12310.
69. A. Odedra, S. Datta, R.-S. Liu, J. Org. Chem. 2007, 72, 3289-3292
70. M. Tobisu, H. Nakai, N. Chatani, J. Org. Chem. 2009, 74, 5471-5475
71. W. H. N. Nijhuis, W. Verboom, A. A. El-Fadl, S. Harkema, D. N. Reinhoudt, J. Org. Chem. 1989, 54, 199-209.
72. S. J. Mahoney, D. T. Moon, J. Hollinger, E. Fillion, Tetrahedron Lett. 2009, 50, 4706-4709.
73. K. Mori, S. Sueoka, T. Akiyama, J. Am. Chem. Soc. 2011, 133, 2424-2426
74. K. Mori, S. Sueoka, T. Akiyama, Chem. Lett. 2011, 40, 1386-1388.
75. S. Murarka, I. Deb, C. Zhang, D. Seidel, J. Am. Chem. Soc. 2009, 131, 13226-13227.
76. W. D. Cao, X. H. Liu, W. T. Wang, L. L. Lin, X. M. Feng, Org. Lett. 2011, 13, 600-603.
77. Y. K. Kang, S. M. Kim, D. Y. Kim, J. Am. Chem. Soc. 2010, 132, 11847-11849.
78. J. F. Austin, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 1172-1173.
79. W. S. Jen, J. J. M. Wiener, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 9874-9875
80. N. A. Paras, D. W. C. MacMillan, J. Am. Chem. Soc. 2001, 123, 4370-4371
81. B. List, P. Pojarliev, C. Castello, Org. Lett. 2001, 3, 573-575
82. N. Halland, R. G. Hazell, K. A. Jørgensen, J. Org. Chem. 2002, 67, 8331-8338.
83. Z. Jiao, S. Zhang, C. He, Y. Tu, S. Wang, F. Zhang, Y. Zhang, H. Li, Angew. Chem. 2012, 124, 8941-8945
84. Angew. Chem. Int. Ed. 2012, 51, 8811-8815.
85. K. Mori, K. Ehara, K. Kurihara, T. Akiyama, J. Am. Chem. Soc. 2011, 133, 6166-6169
86. Y. P. He, Y. L. Du, S. W. Luo, L. Z. Gong, Tetrahedron Lett. 2011, 52, 7064-7066.
87. L. J. Chen, L. Zhang, J. Lv, J. P. Cheng, S. Z. Luo, Chem. Eur. J. 2012, 18, 8891-8895.
88. L. Zhang, L. J. Chen, J. Lv, J. P. Cheng, S. Z. Luo, Chem. Asian J. 2012, 7, 2569-2576.
89. G. Zhou, F. Liu, J. Zhang, Chem. Eur. J. 2011, 17, 3101-3104.
90. V. K.-Y. Lo, M.-K. Wong, C.-M. Che, Org. Lett. 2008, 10, 517-519.
91. J. Kuang, S. Ma, J. Am. Chem. Soc. 2010, 132, 1786-1787.
92. T. Sugiishi, H. Nakamura, J. Am. Chem. Soc. 2012, 134, 2504-2507.
93. B. Bolte, Y. Odabachian, F. Gagosz, J. Am. Chem. Soc. 2010, 132, 7294-7296.
94. X. Gao, V. Gaddam, E. Altenhofer, R. R. Tata, Z. Cai, N. Yongpruksa, A. K. Garimallaprabhakaran, M. Harmata, Angew. Chem. 2012, 124, 7122-7125
95. Angew. Chem. Int. Ed. 2012, 51, 7016-7019.
96. J. C. Ruble, A. R. Hurd, T. A. Johnson, D. A. Sherry, M. R. Barbachyn, P. L. Toogood, G. L. Bundy, D. R. Graber, G. M. Kamilar, J. Am. Chem. Soc. 2009, 131, 3991-3997; 1,5-hydride transfer applied to the synthesis of 3-arylisoquinoline and bridged D -secoestrone azacycles, see
97. K. Mori, T. Kawasaki, T. Akiyama, Org. Lett. 2012, 14, 1436-1439
98. J. Wölfling, E. Frank, G. Schneider, L. F. Tietze, Eur. J. Org. Chem. 2004, 90-100.
99. I. D. Jurberg, B. Peng, E. Wöstefeld, M. Wasserloos, N. Maulide, Angew. Chem. 2012, 124, 1986-1989
100. Angew. Chem. Int. Ed. 2012, 51, 1950-1953.