Deprotonative metalation of aromatic compounds by using an amino-based lithium cuprate

Chemistry - A European Journal

Volumn 17, Issue 37, 2011, Pages 10405-10416

  Nguyen, Tan Tai ^a   Marquise, Nada ^a   Chevallier, Floris ^a   Mongin, Florence ^a  

^a Chimie et Photonique Moleculaires Rennes   (France)

Author keywords

bimetallic bases; copper; deprotonation; lithium; synthesis design

Indexed keywords

ARYL HALIDES; BENZOYL CHLORIDES; BIARYLS; BIMETALLIC BASES; CUPRATES; DIPHENYL DISULFIDE; ELECTROPHILES; GOOD YIELD; IODOMETHANE; METALATIONS; OXIDATIVE AGENTS; SYNTHESIS DESIGN;

CHLORINE COMPOUNDS; COPPER COMPOUNDS; LITHIUM; OPTIMIZATION; THIOPHENE;

LITHIUM COMPOUNDS;

EID: 80052248274     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201100990     Document Type: Article

References (88)

1. H. W. Gschwend, H. R. Rodriguez, Org. React. 1979, 26, 1-360
2. P. Beak, V. Snieckus, Acc. Chem. Res. 1982, 15, 306-312
3. V. Snieckus, Chem. Rev. 1990, 90, 879-933
4. T. G. Gant, A. I. Meyers, Tetrahedron 1994, 50, 2297-2360
5. M. Schlosser, Organometallics in Synthesis: A Manual, 2 nd ed., (Ed.: M. Schlosser,), Wiley, New York, 2002, Chapter 1.
6. R. E. Mulvey, Organometallics 2006, 25, 1060-1075
7. R. E. Mulvey, F. Mongin, M. Uchiyama, Y. Kondo, Angew. Chem. 2007, 119, 3876-3899
8. Angew. Chem. Int. Ed. 2007, 46, 3802-3824
9. S. H. Wunderlich, P. Knochel, Angew. Chem. 2007, 119, 7829-7832
10. Angew. Chem. Int. Ed. 2007, 46, 7685-7688
11. R. E. Mulvey, Acc. Chem. Res. 2009, 42, 743-755
12. S. H. Wunderlich, M. Kienle, P. Knochel, Angew. Chem. 2009, 121, 7392-7396
13. Angew. Chem. Int. Ed. 2009, 48, 7256-7260
14. S. H. Wunderlich, P. Knochel, Angew. Chem. 2009, 121, 9897-9900
15. Angew. Chem. Int. Ed. 2009, 48, 9717-9720.
16. N. Krause, Modern Organocopper Chemistry (Ed.:, N. Krause,), Wiley-VCH, Weinhein, 2002.
17. B. E. Rossiter, N. M. Swingle, Chem. Rev. 1992, 92, 771-806
18. S. H. Bertz, C. A. Ogle, A. Rastogi, J. Am. Chem. Soc. 2005, 127, 1372-1373.
19. S. Usui, Y. Hashimoto, J. V. Morey, A. E. H. Wheatley, M. Uchiyama, J. Am. Chem. Soc. 2007, 129, 15102-15103
20. J. Haywood, J. V. Morey, A. E. H. Wheatley, C.-Y. Liu, S. Yasuike, J. Kurita, M. Uchiyama, P. R. Raithby, Organometallics 2009, 28, 38-41. See also
21. H.-J. Gais, C. V. Rao, R. Loo, Chem. Eur. J. 2008, 14, 6510-6528.
22. A. Seggio, M. I. Lannou, F. Chevallier, D. Nobuto, M. Uchiyama, S. Golhen, T. Roisnel, F. Mongin, Chem. Eur. J. 2007, 13, 9982-9989
23. A. Seggio, F. Chevallier, M. Vaultier, F. Mongin, J. Org. Chem. 2007, 72, 6602-6605
24. J. M. L'Helgoual'ch, A. Seggio, F. Chevallier, M. Yonehara, E. Jeanneau, M. Uchiyama, F. Mongin, J. Org. Chem. 2008, 73, 177-183
25. G. Dayaker, A. Sreeshailam, F. Chevallier, T. Roisnel, P. Radha Krishna, F. Mongin, Chem. Commun. 2010, 46, 2862-2864
26. K. Snégaroff, S. Komagawa, F. Chevallier, P. C. Gros, S. Golhen, T. Roisnel, M. Uchiyama, F. Mongin, Chem. Eur. J. 2010, 16, 8191-8201
27. F. Chevallier, Y. S. Halauko, C. Pecceu, I. F. Nassar, T. U. Dam, T. Roisnel, V. E. Matulis, O. A. Ivashkevich, F. Mongin, Org. Biomol. Chem. 2011, 9, 4671-4684.
28. J. M. L'Helgoual'ch, G. Bentabed-Ababsa, F. Chevallier, M. Yonehara, M. Uchiyama, A. Derdour, F. Mongin, Chem. Commun. 2008, 5375-5377
29. J. M. L'Helgoual'ch, G. Bentabed-Ababsa, F. Chevallier, A. Derdour, F. Mongin, Synthesis 2008, 4033-4035
30. G. Bentabed-Ababsa, F. Blanco, A. Derdour, F. Mongin, F. Trécourt, G. Queguiner, R. Ballesteros, B. Abarca, J. Org. Chem. 2009, 74, 163-169
31. K. Snégaroff, F. Lassagne, G. Bentabed-Ababsa, E. Nassar, S. Cheikh Sid Ely, S. Hesse, E. Perspicace, A. Derdour, F. Mongin, Org. Biomol. Chem. 2009, 7, 4782-4788
32. K. Snégaroff, J. M. L'Helgoual'ch, G. Bentabed-Ababsa, T. T. Nguyen, F. Chevallier, M. Yonehara, M. Uchiyama, A. Derdour, F. Mongin, Chem. Eur. J. 2009, 15, 10280-10290
33. G. Bentabed-Ababsa, S. Cheikh Sid Ely, S. Hesse, E. Nassar, F. Chevallier, T. T. Nguyen, A. Derdour, F. Mongin, J. Org. Chem. 2010, 75, 839-847
34. K. Snégaroff, S. Komagawa, M. Yonehara, F. Chevallier, P. C. Gros, M. Uchiyama, F. Mongin, J. Org. Chem. 2010, 75, 3117-3120
35. A. Sreeshailam, G. Dayaker, F. Chevallier, T. Roisnel, P. Radha Krishna, F. Mongin, Eur. J. Org. Chem. 2011, 17, 3715-3718.
36. LiCl is present in the reaction mixtures, but its presence in the cuprate structures was not proved.
37. I. Bertini, F. Mani, Inorg. Chem. 1967, 6, 2032-2035.
38. T. T. Nguyen, F. Chevallier, V. Jouikov, F. Mongin, Tetrahedron Lett. 2009, 50, 6787-6790.
39. N. Yoshikai, R. Iida, E. Nakamura, Adv. Synth. Catal. 2008, 350, 1063-1072.
40. A. Turck, N. Plé, F. Mongin, G. Queguiner, Tetrahedron 2001, 57, 4489-4505
41. F. Chevallier, F. Mongin, Chem. Soc. Rev. 2008, 37, 595-609.
42. A. Wada, J. Yamamoto, S. Kanatomo, Heterocycles 1987, 26, 585-589
43. A. Wada, J. Yamamoto, Y. Hamaoka, K. Ohki, S. Nagai, S. Kanatomo, J. Heterocycl. Chem. 1990, 27, 1831-1835.
44. R. J. Mattson, C. P. Sloan, J. Org. Chem. 1990, 55, 3410-3412.
45. D. W. Slocum, D. Reed, F. Jackson III, C. Friesen, J. Organomet. Chem. 1996, 512, 265-267
46. D. W. Slocum, A. Carroll, P. Dietzel, S. Eilerman, J. P. Culver, B. McClure, S. Brown, R. W. Holman, Tetrahedron Lett. 2006, 47, 865-868.
47. C. Lambert, P. v. R. Schleyer, Angew. Chem. 1994, 106, 1187-1199
48. Angew. Chem. Int. Ed. Engl. 1994, 33, 1129-1140
49. M. John, C. Auel, C. Behrens, M. Marsch, K. Harms, F. Bosold, R. M. Gschwind, P. R. Rajamohanan, G. Boche, Chem. Eur. J. 2000, 6, 3060-3068
50. A. E. H. Wheatley, New J. Chem. 2004, 28, 435-443.
51. F. Trécourt, M. Mallet, F. Marsais, G. Queguiner, J. Org. Chem. 1988, 53, 1367-1371
52. M. Mallet, J. Organomet. Chem. 1991, 406, 49-56.
53. D. L. Comins, L. A. Morgan, Tetrahedron Lett. 1991, 32, 5919-5922.
54. A. S. C. Chan, C.-C. Chen, R. Cao, M.-R. Lee, S.-M. Peng, G. H. Lee, Organometallics 1997, 16, 3469-3473.
55. P. Gros, Y. Fort, P. Caubère, J. Chem. Soc. Perkin Trans. 1 1997, 3071-3080
56. P. Gros, Y. Fort, G. Queguiner, P. Caubère, Tetrahedron Lett. 1995, 36, 4791-4794.
57. T. Fujisawa, Y. Kurita, M. Kawashima, T. Sato, Chem. Lett. 1982, 1641-1642
58. P. Kocienski, C. Barber, Pure Appl. Chem. 1990, 62, 1933-1940
59. P. Ashworth, B. Broadbelt, P. Jankowski, P. Kocienski, A. Pimm, R. Bell, Synthesis 1995, 199-206.
60. G. Queguiner, F. Marsais, V. Snieckus, J. Epsztajn, Adv. Heterocycl. Chem. 1991, 52, 187-304.
61. A. C. Spivey, L. Shukla, J. F. Hayler, Org. Lett. 2007, 9, 891-894.
62. S. V. Kessar, P. Singh, K. N. Singh, M. Dutt, J. Chem. Soc. Chem. Commun. 1991, 570-571
63. M. Jaric, B. A. Haag, A. Unsinn, K. Karaghiosoff, P. Knochel, Angew. Chem. 2010, 122, 5582-5586
64. Angew. Chem. Int. Ed. 2010, 49, 5451-5455.
65. H. Yamamoto, K. Maruoka, J. Org. Chem. 1980, 45, 2739-2740.
66. S. R. Shengule, P. Karuso, Org. Lett. 2006, 8, 4083-4084.
67. Attempts to use activated alkenes failed.
68. S. R. Dubbaka, M. Kienle, H. Mayr, P. Knochel, Angew. Chem. 2007, 119, 9251-9255
69. Angew. Chem. Int. Ed. 2007, 46, 9093-9096.
70. C. Amatore, E. Carre, A. Jutand, M. A. M'Barki, Organometallics 1995, 14, 1818-1826.
71. V. Bonnet, F. Mongin, F. Trécourt, G. Queguiner, P. Knochel, Tetrahedron Lett. 2001, 42, 5717-5719
72. A. Seggio, A. Jutand, G. Priem, F. Mongin, Synlett 2008, 2955-2960.
73. G. Dayaker, F. Chevallier, P. C. Gros, F. Mongin, Tetrahedron 2010, 66, 8904-8910.
74. T. Güngör, F. Marsais, G. Queguiner, J. Organomet. Chem. 1981, 215, 139-150.
75. F. Trécourt, F. Marsais, T. Güngor, G. Queguiner, J. Chem. Soc. Perkin Trans. 1 1990, 2409-2415.
76. K. Inamoto, M. Katsuno, T. Yoshino, Y. Arai, K. Hiroya, T. Sakamoto, Tetrahedron 2007, 63, 2695-2711.
77. G. L. Beutner, J. T. Kuethe, N. Yasuda, Tetrahedron Lett. 2009, 50, 781-784.
78. X. Chen, M. Yu, M. Wang, J. Chem. Res. 2005, 80-81.
79. C. Waterlot, B. Hasiak, D. Couturier, B. Rigo, Tetrahedron 2001, 57, 4889-4901.
80. M. Ochiai, E. Fujita, M. Arimoto, H. Yamaguchi, Chem. Pharm. Bull. 1982, 30, 3994-3999.
81. M. L. N. Rao, V. Venkatesh, D. Banerjee, Tetrahedron 2007, 63, 12917-12926.
82. M. Arthuis, R. Pontikis, J.-C. Florent, Org. Lett. 2009, 11, 4608-4611.
83. Y. Miyahara, J. Heterocycl. Chem. 1979, 16, 1147-1151.
84. M. Shilai, Y. Kondo, T. Sakamoto, J. Chem. Soc. Perkin Trans. 1 2001, 442-444.
85. N. Boudet, S. R. Dubbaka, P. Knochel, Org. Lett. 2008, 10, 1715-1718.
86. C. A. Fleckenstein, H. Plenio, Chem. Eur. J. 2008, 14, 4267-4279.
87. R. E. DeSchepper, J. S. Swenton, Tetrahedron Lett. 1985, 26, 4831-4834.
88. M. Terashima, K. Seki, C. Yoshida, K. Ohkura, Y. Kanaoka, Chem. Pharm. Bull. 1985, 33, 1009-1015.