Iron-catalyzed hydromagnesiation: Synthesis and characterization of benzylic grignard reagent intermediate and application in the synthesis of ibuprofen

Organometallics

Volumn 33, Issue 20, 2014, Pages 5811-5819

  Greenhalgh, Mark D ^a   Kolodziej, Adam ^a   Sinclair, Fern ^a   Thomas, Stephen P ^a  

^a UNIVERSITY OF EDINBURGH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYLIC; GRIGNARD REAGENT; SYNTHESIS AND CHARACTERIZATIONS;

EID: 84908626492     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om500319h     Document Type: Article

References (106)

1. Bolm, C.; Legros, J.; Le Paih, J.; Zani, L. Chem. Rev. 2004, 104, 6217
2. Enthaler, S.; Junge, K.; Beller, M. Angew. Chem., Int. Ed. 2008, 47, 3317
3. Correa, A.; García Mancheño, O.; Bolm, C. Chem. Soc. Rev. 2008, 37, 1108
4. Iron Catalysis in Organic Chemistry: Reactions and Applications; Pleitker, B., Ed.; Wiley-VCH: Weinheim, Germany, 2008.
5. Risk list 2012; British Geological Survey: Nottingham, U.K., 2012.
6. Kharasch, M. S.; Fuchs, C. F. J. Org. Chem. 1945, 10, 292
7. Tamura, M.; Kochi, J. K. J. Am. Chem. Soc. 1971, 93, 1487
8. Ilies, L.; Nakamura, E. Iron-catalyzed cross-coupling reactions. In The Chemistry of Organoiron Compounds; Marek, I., Ed.; Wiley: Hoboken, NJ, 2014; pp 539-568.
9. Nakamura, E.; Yoshikai, N. J. Org. Chem. 2010, 75, 6061
10. Czaplik, W. M.; Mayer, M.; Cvengroš, J.; Jacobi von Wangelin, A. ChemSusChem 2009, 2, 396
11. Sherry, B. D.; Fürstner, A. Acc. Chem. Res. 2008, 41, 1500
12. Junge, K.; Schröder, K.; Beller, M. Chem. Commun. 2011, 47, 4849
13. Le Bailly, B. A. F.; Thomas, S. P. RSC Adv. 2011, 1, 1435
14. Nakazawa, H.; Itazaki, M. Top. Organomet. Chem. 2011, 33, 27
15. For a review see: Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Rev. 2011, 111, 1293
16. Tewari, N.; Maheshwari, N.; Medhane, R.; Nizar, H.; Prasad, M. Org. Process Res. Dev. 2012, 16, 1566
17. Silverman, G. S.; Rakita, P. E. Handbook of Grignard Reagents; Marcel Decker: New York, 1996.
18. Felkin, H.; Swierczewski, G. Tetrahedron 1975, 31, 2735
19. Sato, F. J. Organomet. Chem. 1985, 285, 53
20. Sato, F.; Urabe, H. Preparation of Grignard Reagents from Olefins and Acetylenes. In Handbook of Grignard Reagents; Silverman, G. S.; Rakita, P. E., Eds.; Marcel Decker: New York, 1996; pp 23-52.
21. Greenhalgh, M. D.; Thomas, S. P. Synlett 2013, 24, 531
22. Podall, H. E.; Foster, W. E. J. Org. Chem. 1958, 23, 1848
23. Ashby, E. C.; Smith, T. J. Chem. Soc., Chem. Commun. 1978, 30
24. Bogdanovic, B.; Schwickardi, M.; Sikorsky, P. Angew. Chem., Int. Ed. Engl. 1982, 21, 199
25. Finkbeiner, H. L.; Cooper, G. D. J. Org. Chem. 1961, 26, 4779
26. Cooper, G. D.; Finkbeiner, H. L. J. Org. Chem. 1962, 27, 1493
27. Finkbeiner, H. L.; Cooper, G. D. J. Org. Chem. 1962, 27, 3395
28. Farády, L.; Bencze, L.; Markó, L. J. Organomet. Chem. 1967, 10, 505
29. Farády, L.; Bencze, L.; Markó, L. J. Organomet. Chem. 1969, 17, 107
30. Tamura, M.; Kochi, J. Bull. Chem. Soc. Jpn. 1971, 44, 3063
31. Sato, F.; Ishikawa, H.; Sato, M. Tetrahedron Lett. 1980, 21, 365
32. Colomer, E.; Corriu, R. J. Organomet. Chem. 1974, 82, 367
33. Ashby, E. C.; Ainslie, R. D. J. Organomet. Chem. 1983, 250, 1
34. Shirakawa, E.; Ikeda, D.; Masui, S.; Yoshida, M.; Hayashi, T. J. Am. Chem. Soc. 2012, 134, 272
35. Greenhalgh, M. D.; Thomas, S. P. J. Am. Chem. Soc. 2012, 134, 11900
36. Ilies, L.; Yoshida, T.; Nakamura, E. J. Am. Chem. Soc. 2012, 134, 16951
37. Tamura, M.; Kochi, J. J. Organomet. Chem. 1971, 31, 289
38. Shirakawa, E.; Yamagami, T.; Kimura, T.; Yamaguchi, S.; Hayashi, T. J. Am. Chem. Soc. 2005, 127, 17164
39. Zhang, D.; Ready, J. M. J. Am. Chem. Soc. 2006, 128, 15050
40. Yamagami, T.; Shintani, R.; Shirakawa, E.; Hayashi, T. Org. Lett. 2007, 9, 1045
41. Shirakawa, E.; Ikeda, D.; Yamagami, T.; Hayashi, T. Chem. Commun. 2008, 1214
42. Hata, T.; Sujaku, S.; Hirone, N.; Nakano, K.; Imoto, J.; Imade, H.; Urabe, H. Chem. Eur. J. 2011, 17, 14593
43. Yu, D.-G.; Wang, X.; Zhu, R.-Y.; Luo, S.; Zhang, X.-B.; Wang, B.-Q.; Wang, L.; Shi, Z.-J. J. Am. Chem. Soc. 2012, 134, 14638
44. Luo, S.; Yu, D.-G.; Zhu, R.-Y.; Wang, X.; Wang, L.; Shi, Z.-J. Chem. Commun. 2013, 49, 7794
45. Hirao, A.; Loykulnant, S.; Ishizone, T. Prog. Polym. Sci. 2002, 27, 1399
46. Gibson, V. C.; Redshaw, C.; Solan, G. A. Chem. Rev. 2007, 107, 1745
47. Gibson, V. C.; Solan, G. A. Top. Organomet. Chem. 2009, 26, 107
48. Ashby, E. C.; Laemmle, J.; Neumann, H. M. Acc. Chem. Res. 1974, 7, 272
49. Walker, F. W.; Ashby, E. C. J. Am. Chem. Soc. 1969, 91, 3845
50. Smith, M. B.; Becker, W. E. Tetrahedron 1967, 23, 4215
51. Ashby, E. C.; Becker, W. E. J. Am. Chem. Soc. 1963, 85, 118
52. Parris, G. E.; Ashby, E. C. J. Am. Chem. Soc. 1971, 93, 1206
53. 13C NMR spectroscopy see: Baker, K. V.; Brown, J. M.; Hughes, N.; Skarnulis, A. J.; Sexton, A. J. Org. Chem. 1991, 56, 698
54. Schlenk, W.; Schlenk, W. Ber. dtsch. Chem. Ges. 1929, 62, 920
55. Noller, C. R.; White, W. R. J. Am. Chem. Soc. 1937, 59, 1354
56. Ibuprofen: A Critical Bibliographic Review; Rainsford, K. D., Ed.; Taylor & Francis: London, 1999.
57. Nicholson, J. S.; Adams, S. S. GB Pat. 971,700, 1964; US Pat. 3228831 A, 1966; US Pat 3385886, 1968.
58. Elango, V.; Murphy, M. A.; Smith, B. L.; Davenport, K. G.; Mott, G. N.; Zey, E. G.; Moss, G. L. US Pat. 4981995, 1991.
59. Shang, R.; Fu, Y.; Liu, L. CN Pat. 102010323 A, 2011.
60. McQuade, D. T.; Bogdan, A.; Poe, S. L. US Pat. 20110054208 A1, 2011.
61. Chaudhari, R. V.; Seayad, A.; Jayasree, S. US Pat. 20050283020 A1, 2005.
62. Mayahara, K.; Inoue, T.; Mori, T.; Tamai, H. Jpn. Pat. 2002371030 A, 2002.
63. Chaudhari, R. V.; Seayad, A.; Jayasree, S. US Pat. 6093847 A, 2000.
64. Wu, T.-C. World Pat. 2000035849, 2000.
65. Sheldon, R. A.; Matt, L.; Papadogianakis, G. US Pat. 5536874, 1996.
66. Correa, A.; León, T.; Martin, R. J. Am. Chem. Soc. 2014, 136, 1062
67. León, T.; Correa, A.; Martin, R. J. Am. Chem. Soc. 2013, 135, 1221
68. Hama, T.; Ge, S.; Hartwig, J. F. J. Org. Chem. 2013, 78, 8250
69. Metzger, A.; Bernhardt, S.; Manolikakes, G.; Knochel, P. Angew. Chem., Int. Ed. 2010, 49, 4665
70. Bogdan, A. R.; Poe, S. L.; Kubis, D. C.; Broadwater, S. J.; McQuade, D. T. Angew. Chem., Int. Ed. 2009, 48, 8547
71. Frew, J. J. R.; Damian, K.; Van Rensburg, H.; Slawin, A. M. Z.; Tooze, R. P.; Clarke, M. L. Chem. - Eur. J. 2009, 15, 10504
72. Aramini, A.; Sablone, M. R.; Bianchini, G.; Amore, A.; Fani, M.; Perrone, P.; Dolce, A.; Allegretti, M. Tetrahedron 2009, 65, 2015
73. Ooka, H.; Inoue, T.; Itsuno, S.; Tanaka, M. Chem. Commun. 2005, 1173
74. Lee, S.; Beare, N. A.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 8410
75. Moradi, W. A.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7996
76. Gooßen, L. J. Chem. Commun. 2001, 669
77. Neumann, S. M.; Kochi, J. K. J. Org. Chem. 1975, 40, 599
78. Felkin, H.; Meunier, B. J. Organomet. Chem. 1978, 146, 169
79. Molander, G. A.; Rahn, B. J.; Shubert, D. C. Tetrahedron Lett. 1983, 24, 5449
80. Fürstner, A.; Brunner, H. Tetrahedron Lett. 1996, 37, 700
81. Dohle, W.; Kopp, F.; Cahiez, G.; Knochel, P. Synlett 2001, 1901
82. Scheiper, B.; Bonnekessel, M.; Krause, H.; Fürstner, A. J. Org. Chem. 2004, 69, 3943
83. Itami, K.; Higashi, S.; Mineno, M.; Yoshida, J.-I. Org. Lett. 2005, 7, 1219
84. Dunet, G.; Knochel, P. Synlett 2006, 407
85. Le Bailly, B. A. F.; Greenhalgh, M. D.; Thomas, S. P. Chem. Commun. 2012, 48, 1580
86. Frank, D. F.; Guiet, L.; Käslin, A.; Murphy, E.; Thomas, S. P. RSC Adv. 2013, 3, 25698
87. Czaplik, W. M.; Mayer, M.; Jacobi von Wangelin, A. ChemCatChem 2011, 3, 135
88. Czaplik, W. M.; Grupe, S.; Mayer, M.; Jacobi von Wangelin, A. Chem. Commun. 2010, 46, 6350
89. Gülak, S.; Gieshoff, T. N.; Jacobi von Wangelin, A. Adv. Synth. Catal. 2013, 355, 2197
90. Cahiez, G.; Kabiak, V.; Duplais, C.; Moyeux, A. Angew. Chem., Int. Ed. 2007, 46, 4364
91. Nakamura, M.; Matsuo, K.; Ito, S.; Nakamura, E. J. Am. Chem. Soc. 2004, 126, 3686
92. Fürstner, A.; Leitner, A. Angew. Chem., Int. Ed. 2002, 41, 609
93. Yoshikai, N.; Mieczkowski, A.; Matsumoto, A.; Ilies, L.; Nakamura, E. J. Am. Chem. Soc. 2010, 132, 5568
94. Knochel, P.; Dohle, W.; Gommermann, N.; Kneisel, F. F.; Kopp, F.; Korn, T.; Sapountzis, I.; Vu, V.-A. Angew. Chem., Int. Ed. 2003, 42, 4302
95. Welther, A.; Bauer, M.; Mayer, M.; Jacobi von Wangelin, A. ChemCatChem 2012, 4, 1088
96. Cahiez, G.; Avedissian, H. Synthesis 1998, 1199
97. Larsen, U. S.; Martiny, L.; Begtrup, M. Tetrahedron Lett. 2005, 46, 4261
98. Cahiez, G.; Habiak, V.; Gager, O. Org. Lett. 2008, 10, 2389
99. Cahiez, G.; Gager, O.; Habiak, V. Synthesis 2008, 16, 2636
100. Li, B.-J.; Wu, Z.-H.; Guan, B.-T.; Sun, C.-L.; Wang, B.-Q.; Shi, Z.-J. J. Am. Chem. Soc. 2009, 131, 14656
101. Small, B. L.; Brookhart, M.; Bennett, A. M. A. J. Am. Chem. Soc. 1998, 120, 4049
102. Nugent, W. A.; McKinney, R. J. J. Org. Chem. 1985, 50, 5370
103. Smith, C. R.; RajunBabu, T. V. Tetrahedron 2010, 66, 1102
104. Frantz, D. E.; Weaver, D. G.; Carey, J. P.; Kress, M. H.; Dolling, U. H. Org. Lett. 2002, 4, 4717
105. Chung, C. W. Y.; Toy, P. H. Tetrahedron 2005, 61, 709
106. O'Connell, J. L.; Simpson, J. S.; Dumanski, P. G.; Simpson, G. W.; Easton, C. J. Org. Biomol. Chem. 2006, 4, 2716