Continuous preparation of arylmagnesium reagents in flow with inline IR monitoring

Organic Process Research and Development

Volumn 16, Issue 5, 2012, Pages 1102-1113

  Brodmann, Tobias ^a   Koos, Peter ^a   Metzger, Albrecht ^a   Knochel, Paul ^b   Ley, Steven V ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ANALYTICAL TOOL; ARYL IODIDES; BY-PRODUCT FORMATION; CHEMICAL PROCESSING; CONTINUOUS FLOWS; CONTINUOUS-FLOW SYSTEM; EXCHANGE REACTION; FLOW CELLS; FUNCTIONALIZED; GRIGNARD; IN-LINE; MICRO-SCALES; POTENTIAL TOOL;

BROMINE COMPOUNDS; CHEMICAL INDUSTRY;

CHEMICAL REACTIONS;

EID: 84862064868     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op200275d     Document Type: Article

References (71)

1. Grignard, V. C. R. Acad. Sci. 1900, 130, 1222-1325
2. Silverman, G. S.; Rakita, P. E., Eds. Handbook of Grignard Reagents; Marcel Dekker: New York, NY, 1996.
3. Wakefield, B. J. Organomagnesium Methods in Organic Synthesis; Academic Press: London, 1995. Richey, H. G., Jr., Ed. Grignard Reagents: New Development; Wiley: New York, NY, 1999.
4. Boudier, A.; Bromm, L. O.; Lotz, M.; Knochel, P. Angew. Chem., Int. Ed. 2000, 39, 4414-4435
5. Knochel, P.; Leuser, H.; Gong, Z.-L.; Perrone, S.; Kneisel, F. F., Eds. Handbook of Functionalized Organometallics; Wiley-VCH: Weinheim, 2005, 251. Knochel, P.; Millot, N.; Rodriguez, A. L.; Tucker, C. E. Organic Reactions; Wiley: New York, 2001.
6. Garst, J. F.; Soriaga, M. P. Coord. Chem. Rev. 2004, 248, 623-652
7. Harrington, P. J.; Lodewijk, E. Org. Process Res. Dev. 1997, 1, 72-76
8. Wegner, J.; Ceylan, S.; Kirschning, A. Chem. Commun. 2011, 47, 4583
9. Webb, D.; Jamison, T. F. Chem. Sci. 2010, 1, 675
10. Wiles, C.; Watts, P. Chem. Commun. 2011, 47, 6512
11. Baxendale, I. R.; Hayward, J. J.; Lanners, S.; Ley, S. V.; Smith, C. D. In Microreactors in Organic Synthesis and Catalysis; Wirth, T., Ed.; Wiley: New York, 2008.
12. Yoshida, J. I. Chem. Rec. 2010, 10, 332
13. Nagaki, A.; Takizawa, E.; Yoshida, J. Chem.-Eur. J. 2010, 16, 14149
14. Mak, X. Y.; Laurino, P.; Seeberger, P. H. Beilstein J. Org. Chem. 2009, 5, 19
15. Razzaq, T.; Kappe, C. O. Chem.-Asian J. 2010, 5, 1274
16. Hessel, V. Chem. Eng. Technol. 2009, 32, 1655
17. Hook, B. D. A.; Dohle, W.; Hirst, P. R.; Pickworth, M.; Berry, M. B.; Booker-Milburn, K. I. J. Org. Chem. 2005, 70, 7558
18. Bogdan, A. R.; Poe, S. L.; Kubis, D. C.; Broadwater, S. J.; McQuade, D. T. Angew. Chem., Int. Ed. 2009, 48, 8547
19. Bogdan, A. R.; Sach, N. W. Adv. Synth. Catal. 2009, 351, 849
20. Brasholz, M.; Johnson, B. A.; Macdonald, J. M.; Polyzos, A.; Tsanaktsidis, J.; Saubern, S.; Holmes, A. B.; Ryan, J. H. Tetrahedron 2010, 66, 6445
21. Nieuwland, P. J.; Koch, K.; van Harskamp, N.; Wehrens, R.; van Hest, J. C. M.; Rutjes, F. Chem.-Asian J. 2010, 5, 799
22. Ahmed-Omer, B.; Brandt, J. C.; Wirth, T. Org. Biomol. Chem. 2007, 5, 733
23. Brandt, J. C.; Wirth, T. Beilstein J. Org. Chem. 2009, 5, 30
24. Murphy, E. R.; Martinelli, J. R.; Zaborenko, N.; Buchwald, S. L.; Jensen, K. F. Angew. Chem., Int. Ed. 2007, 46, 1734
25. Chambers, R. D.; Fox, M. A.; Sandford, G.; Trmcic, J.; Goeta, A. J. Fluor. Chem. 2007, 128, 29
26. Fukuyama, T.; Rahman, T.; Kamata, N.; Ryu, I. Beilstein J. Org. Chem. 2009, 5, 34
27. Miller, P. W.; Jennings, L. E.; deMello, A. J.; Gee, A. D.; Long, N. J.; Vilar, R. Adv. Synth. Catal. 2009, 351, 3260
28. Kobayashi, J.; Mori, Y.; Okamoto, K.; Akiyama, R.; Ueno, M.; Kitamori, T.; Kobayashi, S. Science 2004, 304, 1305
29. Wakami, H.; Yoshida J. Org. Process Res. Dev. 2005, 9, 787-791
30. Kim, H.; Nagaki, A.; Yoshida, J. Nat. Commun. 2011, 2, 1-6
31. Nagaki, A.; Yamada, S.; Doi, M.; Tomida, Y.; Takabayashi, N.; Yoshida, J. Green Chem. 2011, 13, 1110-1113
32. Carter, C. F.; Lange, H.; Ley, S. V.; Baxendale, I. R.; Wittkamp, B.; Goode, J. G.; Gaunt, N. L. Org. Process Res. Dev. 2010, 14, 393-404
33. Mozharov, S.; Nordon, A.; Littlejohn, D.; Wiles, C.; Watts, P.; Dallin, P.; Girkin, J. M. J. Am. Chem. Soc. 2011, 133, 3601-3608
34. Qian, Z.; Baxendale, I. R.; Ley, S. V. Chem.-Eur. J. 2010, 16, 12342-12348
35. Riva, E.; Gagliardi, S.; Martinelli, M.; Passarella, D.; Vigo, D.; Rencurosi, A. Tetrahedron 2010, 66, 3242-3247
36. Polyzos, A.; O'Brien, M.; Petersen, T. P.; Baxendale, I. R.; Ley, S. V. Angew. Chem., Int. Ed. 2010, 50, 1190-1193
37. Rieke, R. D. Science 1989, 246, 1260-1264
38. Burns, T. P.; Rieke, R. D. J. Org. Chem. 1987, 52, 3674-3680
39. Lee, J.; Velarde-Ortiz, R.; Guijarro, A.; Wurst, J. R.; Rieke, R. D. J. Org. Chem. 2000, 65, 5428-5430
40. Knochel, P.; Dohle, W.; Gommermann, N.; Kneisel, F. F.; Kopp, F.; Korn, T.; Sapountzis, I.; Vu, V. A. Angew. Chem., Int. Ed. 2003, 42, 4302-4320
41. Normant, J. F.; Alexakis, A. Synthesis 1981, 841-870
42. Rao, S. A.; Knochel, P. J. Am. Chem. Soc. 1991, 113, 5735-5741
43. Trost, B. M. Chem.-Eur. J. 1998, 4, 2405-2412
44. Mattesonin, D. S. The Chemistry of the Metal-Carbon Bond, Vol. 4, (Ed.: Hartley, F. R.), Wiley, New York, 1987, 307-409.
45. Zhang, M.-X.; Eaton, P. E. Angew. Chem., Int. Ed. 2002, 41, 2169-2171
46. Hoppe, D.; Heuse, T. Angew. Chem., Int. Ed. 1997, 36, 2282-2316
47. Johnson, T. A.; Curtis, M. D.; Beak, P. Org. Lett. 2002, 4, 2747-2749
48. Beak, P.; Anderson, D. R.; Curtis, M. D.; Laumer, J. M.; Pippel, D. J.; Weisenburger, G. A. Acc. Chem. Res. 2000, 33, 715-727
49. Norsikian, S.; Marek, I.; Normant, J.-F. Tetrahedron Lett. 1997, 38, 7523-7526
50. Metallinos, C.; Snieckus, V. Org. Lett. 2002, 4, 1935-1938
51. Snieckus, V. Chem. Rev. 1990, 90, 879-933
52. Piller, F. M.; Appukkuttan, P.; Gavryushin, A.; Helm, M.; Knochel., P. Angew. Chem., Int. Ed. 2008, 47, 6802-6806
53. Krasovskiy, A.; Krasovskaya, V.; Knochel, P. Angew. Chem., Int. Ed. 2006, 45, 2958-2961
54. Lin, W.; Baron, O.; Knochel, P. Org. Lett. 2006, 8, 5673-5676
55. Krasovskiy, A.; Knochel, P. Angew. Chem., Int. Ed. 2004, 43, 3333-3336
56. Krasovskiy, A.; Straub, B.; Knochel, P. Angew. Chem., Int. Ed. 2006, 45, 159-162
57. Ren, H.; Krasovskiy, A.; Knochel, P. Org. Lett. 2004, 6, 4215-4217
58. Ren, H.; Krasovskiy, A.; Knochel, P. Chem. Commun. 2005, 4, 543-545
59. Kopp, F.; Krasovskiy, A.; Knochel, P. Chem. Commun. 2004, 2288-2289
60. Kopp, F.; Knochel, P. Org. Lett. 2007, 9, 1639-1641
61. Kopp, F.; Wunderlich, S.; Knochel, P. Chem. Commun. 2007, 20, 2075-2077
62. Am Ende, D. J.; Clifford, P. J.; DeAntonis, D. M.; SantaMaria, C.; Brenek, S. J. Org. Process Res. Dev. 1999, 3, 319-329
63. Wiss, J.; Ermini, G. Org. Process Res. Dev. 2006, 10, 1082-1286
64. Ende, D. J.; Clifford, P. J.; DeAntoins, D. M.; SantaMaria, C.; Brenek, S. J. Org. Process Res. Dev. 1999, 3, 319-329
65. Lange, H.; Carter, C. F.; Hopkin, M. D.; Burke, A.; Goode, J. G.; Baxendale, I. R.; Ley, S. V. Chem. Sci. 2011, 2, 765-769
66. Sassian, M.; Panov, D.; Tuulmets, A. Appl. Organometal. Chem. 2002, 16, 525-529
67. Tuulmets, A.; Panov, D. J. Organomet. Chem. 1999, 575, 182-186
68. Tuulmets, A.; Mikk, M.; Panov, D. J. Organomet. Chem. 1996, 523, 133-138
69. Krasovskiy, A.; Kopp, F.; Knochel, P. Angew. Chem., Int. Ed. 2006, 45, 497-500
70. Abarbri, M.; Dehmel, F.; Knochel, P. Tetrahedron Lett. 1999, 40, 7449-7453
71. Inoue, A.; Kitagawa, K.; Shinokubo, H.; Oshima, K. J. Org. Chem. 2001, 66, 4333-4339