Cross-coupling of aryllithiums with aryl and vinyl halides in flow microreactors

Chemistry - An Asian Journal

Volumn 7, Issue 5, 2012, Pages 1061-1068

  Nagaki, Aiichiro ^a   Moriwaki, Yuya ^a   Haraki, Suguru ^a   Kenmoku, Akira ^b   Takabayashi, Naofumi ^a   Hayashi, Atsushi ^a   Yoshida, Jun Ichi ^a  

^a KYOTO UNIVERSITY   (Japan)

^b Research Association of Micro Chemical Process Technology (MCPT)   (Japan)

Author keywords

arenes; cross coupling; halides; lithiation; microreactors

Indexed keywords

ARENES; CROSS-COUPLINGS; HALIDES; LITHIATION; MICRO REACTOR;

CHEMICAL REACTORS; INTEGRATION; LIGANDS;

CHEMICAL REACTIONS;

AROMATIC HYDROCARBON; HALOGEN; LIGAND; LITHIUM DERIVATIVE; PALLADIUM; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; SYNTHESIS;

CATALYSIS; HALOGENS; HYDROCARBONS, AROMATIC; LIGANDS; LITHIUM COMPOUNDS; PALLADIUM; VINYL COMPOUNDS;

EID: 84860486213     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201101019     Document Type: Article

References (118)

1. F. Diederich, P. J. Eds. Stang, Metal-catalyzed cross-coupling reactions; Wiley-VCH, New York, 1998
2. S. P. Stanforth, Tetrahedron 1998, 54, 263
3. J. Hassan, M. Sévignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 2002, 102, 1359.
4. A. Suzuki, Angew. Chem. 2011, 123, 6854
5. Angew. Chem. Int. Ed. 2011, 50, 6722.
6. For a review, see:, S. I. Murahashi, J. Organomet. Chem. 2002, 653, 27.
7. S. I. Murahashi, Y. Tanba, M. Yamamura, I. Moritani, Tetrahedron Lett. 1974, 15, 3749
8. S. I. Murahashi, Y. Tanba, M. Yamamura, N. Yoshimura, J. Org. Chem. 1978, 43, 4099.
9. For examples of catalytic processes, see:, S. I. Murahashi, M. Yamamura, K. Yanagisawa, N. Mita, K. Kondo, J. Org. Chem. 1979, 44, 2408.
10. P. Knochel, A. Krasovskiy, I. Sapountzis, in Handbook of Functionalized Organometallics (Ed.:, P. Knochel,), Wiley-VCH, Weinheim, 2005
11. G. Cahiez, A. Moyeux, J. Buendia, C. Duplais, J. Am. Chem. Soc. 2007, 129, 13788
12. S. Sase, M. Jaric, A. Metzger, V. Malakhov, P. Knochel, J. Org. Chem. 2008, 73, 7380
13. G. Cahiez, L. Foulgoc, A. Moyeux, Angew. Chem. 2009, 121, 3013
14. Angew. Chem. Int. Ed. 2009, 48, 2969
15. G. Cahiez, C. Chaboche, C. Duplais, A. Moyeux, Org. Lett. 2009, 11, 277.
16. S. P. Maddaford, B. A. Keay, J. Org. Chem. 1994, 59, 6501
17. N. G. Andersen, S. P. Maddaford, B. A. Keay, J. Org. Chem. 1996, 61, 9556
18. S. D. Brown, R. W. Armstrong, J. Am. Chem. Soc. 1996, 118, 6331
19. A. Carbonnelle, J. Zhu, Org. Lett. 2000, 2, 3477
20. L. Zhu, J. Duquette, M. Zhang, J. Org. Chem. 2003, 68, 3729. However, catalyzed borylation may not be suitable for large-scale synthesis, see
21. W. Li, D. P. Nelson, M. S. Jensen, R. S. Hoerrner, D. Cai, R. D. Larsen, P. J. Reider, J. Org. Chem. 2002, 67, 5394.
22. W. Ehrfeld, V. Hessel, H. Löwe, Microreactors, Wiley-VCH, Weinheim, 2000
23. V. Hessel, S. Hardt, H. Löwe, Chemical Micro Process Engineering, Wiley-VCH, Weinheim, 2004
24. J. Yoshida, Flash Chemistry. Fast Organic Synthesis in Microsystems, Wiley-Blackwell, 2008
25. V. Hessel, A. Renken, J. C. Schouten, J. Yoshida, Micro Precess Engineering, Wiley-Blackwell, 2009.
26. K. Jähnisch, V. Hessel, H. Löwe, M. Baerns, Angew. Chem. 2004, 116, 410
27. Angew. Chem. Int. Ed. 2004, 43, 406
28. G. N. Doku, W. Verboom, D. N. Reinhoudt, A. van den Berg, Tetrahedron 2005, 61, 2733
29. J. Yoshida, A. Nagaki, T. Iwasaki, S. Suga, Chem. Eng. Technol. 2005, 28, 259
30. P. Watts, S. J. Haswell, Chem. Soc. Rev. 2005, 34, 235
31. K. Geyer, J. D. C. Codee, P. H. Seeberger, Chem. Eur. J. 2006, 12, 8434
32. A. J. deMello, Nature 2006, 442, 394
33. H. Song, D. L. Chen, R. F. Ismagilov, Angew. Chem. 2006, 118, 7494
34. Angew. Chem. Int. Ed. 2006, 45, 7336
35. J. Kobayashi, Y. Mori, S. Kobayashi, Chem. Asian J. 2006, 1, 22
36. M. Brivio, W. Verboom, D. N. Reinhoudt, Lab Chip 2006, 6, 329
37. B. P. Mason, K. E. Price, J. L. Steinbacher, A. R. Bogdan, D. T. McQuade, Chem. Rev. 2007, 107, 2300
38. B. Ahmed-Omer, J. C. Brandtand, T. Wirth, Org. Biomol. Chem. 2007, 5, 733
39. P. Watts, C. Wiles, Chem. Commun. 2007, 443
40. T. Fukuyama, M. T. Rahman, M. Sato, I. Ryu, Synlett 2008, 151
41. J. Yoshida, A. Nagaki, T. Yamada, Chem. Eur. J. 2008, 14, 7450
42. R. L. Hartman, K. F. Jensen, Lab Chip 2009, 9, 2495
43. J. P. McMullen, K. F. Jensen, Annu. Rev. Anal. Chem. 2010, 3, 19
44. J. Yoshida, H. Kim, A. Nagaki, ChemSusChem 2011, 4, 331.
45. A. Nagaki, K. Kawamura, S. Suga, T. Ando, M. Sawamoto, J. Yoshida, J. Am. Chem. Soc. 2004, 126, 14702
46. A. Nagaki, M. Togai, S. Suga, N. Aoki, K. Mae, J. Yoshida, J. Am. Chem. Soc. 2005, 127, 11666
47. P. He, P. Watts, F. Marken, S. J. Haswell, Angew. Chem. 2006, 118, 4252
48. Angew. Chem. Int. Ed. 2006, 45, 4146
49. K. Tanaka, S. Motomatsu, K. Koyama, S. Tanaka, K. Fukase, Org. Lett. 2007, 9, 299
50. H. R. Sahoo, J. G. Kralj, K. F. Jensen, Angew. Chem. 2007, 119, 5806
51. Angew. Chem. Int. Ed. 2007, 46, 5704
52. C. H. Hornung, M. R. Mackley, I. R. Baxendale, S. V. Ley, Org. Process Res. Dev. 2007, 11, 399
53. T. Fukuyama, M. Kobayashi, M. T. Rahman, N. Kamata, I. Ryu, Org. Lett. 2008, 10, 533
54. C. Wiles, P. Watts, Org. Process Res. Dev. 2008, 12, 1001
55. A. Nagaki, E. Takizawa, J. Yoshida, J. Am. Chem. Soc. 2009, 131, 1654
56. A. Nagaki, E. Takizawa, J. Yoshida, Chem. Lett. 2009, 38, 486
57. I. C. Wienhöfer, A. Studer, M. T. Rahman, T. Fukuyama, I. Ryu, Org. Lett. 2009, 11, 2457
58. A. R. Bogdan, S. L. Poe, D. C. Kubis, S. J. Broadwater, D. T. McQuade, Angew. Chem. 2009, 121, 8699
59. Angew. Chem. Int. Ed. 2009, 48, 8547.
60. H. Usutani, Y. Tomida, A. Nagaki, H. Okamoto, T. Nokami, J. Yoshida, J. Am. Chem. Soc. 2007, 129, 3046
61. A. Nagaki, Y. Tomida, H. Usutani, H. Kim, N. Takabayashi, T. Nokami, H. Okamoto, J. Yoshida, Chem. Asian J. 2007, 2, 1513
62. A. Nagaki, N. Takabayashi, Y. Tomida, J. Yoshida, Org. Lett. 2008, 10, 3937
63. A. Nagaki, H. Kim, J. Yoshida, Angew. Chem. 2008, 120, 7951
64. Angew. Chem. Int. Ed. 2008, 47, 7833
65. A. Nagaki, N. Takabayashi, Y. Tomida, J. Yoshida, Beilstein J. Org. Chem. 2009, 5, 1
66. Y. Tomida, A. Nagaki, J. Yoshida, Org. Lett. 2009, 11, 3614
67. A. Nagaki, H. Kim, J. Yoshida, Angew. Chem. 2009, 121, 8207
68. Angew. Chem. Int. Ed. 2009, 48, 8063
69. A. Nagaki, E. Takizawa, J. Yoshida, Chem. Eur. J. 2010, 16, 14149
70. A. Nagaki, H. Kim, Y. Moriwaki, C. Matsuo, J. Yoshida, Chem. Eur. J. 2010, 16, 11167
71. Y. Tomida, A. Nagaki, J. Yoshida, J. Am. Chem. Soc. 2011, 133, 3744
72. A. Nagaki, H. Kim, C. Matuo, J. Yoshida, Org. Biomol. Chem. 2010, 8, 1212
73. H. Kim, A. Nagaki, J. Yoshida, Nat. Commun. 2011, 2, 264
74. A. Nagaki, S. Yamada, M. Doi, Y. Tomida, N. Takabayashi, J. Yoshida, Green Chem. 2011, 13, 1110.
75. T. A. Cernak, T. H. Lambert, J. Am. Chem. Soc. 2009, 131, 3124
76. I. R. Baxendale, S. C. Schou, J. Sedelmeier, S. V. Ley, Chem. Eur. J. 2010, 16, 89
77. A. Kirschning, S. Wladimir, M. Klaas, Chem. Eur. J. 2006, 12, 5972
78. J. Wang, G. Sui, V. P. Mocharla, R. J. Lin, M. E. Phelps, H. C. Kolb, H. R. Tseng, Angew. Chem. 2006, 118, 5402
79. Angew. Chem. Int. Ed. 2006, 45, 5276.
80. C. de Bellefon, N. Tanchoux, S. Caravieilhes, P. Grenouillet, V. Hessel, Angew. Chem. 2000, 112, 3584
81. Angew. Chem. Int. Ed. 2000, 39, 3442
82. G. M. S. Greenway, J. Haswell, D. O. Morgan, V. Skelton, P. String, Sens. Actuators B 2000, 63, 153
83. S. J. Haswell, B. O'Sullivan, P. Styring, Lab Chip 2001, 1, 164
84. S. Niwa, M. Eswaramoorthy, J. Nair, A. Raj, N. Itoh, H. Shoji, T. Namba, F. Mizukami, Science 2002, 295, 105
85. T. Fukuyama, M. Shinmen, S. Nishitani, M. Sato, I. Ryu, Org. Lett. 2002, 4, 1691
86. G. Jas, A. Kirschning, Chem. Eur. J. 2003, 9, 5708
87. J. Kobayashi, Y. Mori, K. Okamoto, R. Akiyama, M. Ueno, T. Kitamori, S. Kobayashi, Science 2004, 304, 1305
88. C. Basheer, F. S. J. Hussain, H. K. Lee, S. Valiyaveettil, Tetrahedron Lett. 2004, 45, 7297
89. S. Liu, T. Fukuyama, M. Sato, I. Ryu, Org. Process Res. Dev. 2004, 8, 477
90. U. Kunz, H. Schönfeld, W. Solodenko, G. Jas, A. Kirschning, Ind. Eng. Chem. Res. 2005, 44, 8458
91. E. Comer, M. G. Organ, J. Am. Chem. Soc. 2005, 127, 8160
92. C. K. Y. Lee, A. B. Holmes, S. V. Ley, I. F. McConvey, B. Al-Duri, G. A. Leeke, R. C. D. Santosd, J. P. K. Sevilled, Chem. Commun. 2005, 2175
93. C. Mauger, O. Buisine, S. Caravieilhes, G. Mignani, J. Organomet. Chem. 2005, 690, 3627
94. Y. Uozumi, Y. M. A. Yamada, T. Beppu, N. Fukuyama, M. Ueno, T. Kitamori, J. Am. Chem. Soc. 2006, 128, 15994
95. G. Shore, S. Morin, M. G. Organ, Angew. Chem. 2006, 118, 2827
96. Angew. Chem. Int. Ed. 2006, 45, 2761
97. G. Shi, F. Hong, Q. Liang, H. Fang, S. Nelson, S. G. Weber, Anal. Chem. 2006, 78, 1972
98. M. T. Rahman, T. Fukuyama, N. Kamata, M. Sato, I. Ryu, Chem. Commun. 2006, 2236
99. E. R. Murphy, J. R. Martinelli, N. Zaborenko, S. L. Buchwald, K. F. Jensen, Angew. Chem. 2007, 119, 1764
100. Angew. Chem. Int. Ed. 2007, 46, 1734
101. H. Kawanami, K. Matsushima, M. Sato, Y. Ikushima, Angew. Chem. 2007, 119, 5221
102. Angew. Chem. Int. Ed. 2007, 46, 5129
103. Y. M. A. Yamada, T. Watanabe, K. Torii, Y. Uozumi, Chem. Commun. 2009, 5594
104. J. Jin, M.-M. Cai, J.-X. Li, Synlett 2009, 15, 2534
105. B. Ahmed-Omer, D. A. Barrow, T. Wirth, Tetrahedron Lett. 2009, 50, 3352.
106. S. Suga, D. Yamada, J. Yoshida, Chem. Lett. 2010, 39, 404
107. J. Yoshida, K. Saito, T. Nokami, A. Nagaki, Synlett 2011, 1189.
108. A. Nagaki, A. Kenmoku, Y. Moriwaki, A. Hayashi, J. Yoshida, Angew. Chem. 2010, 122, 7705
109. Angew. Chem. Int. Ed. 2010, 49, 7543.
110. E. I. Negishi, T. Takahashi, S. Baba, S. B. Van Horn, N. Okukado, J. Am. Chem. Soc. 1987, 109, 2393.
111. J. P. Wolfe, R. A. Singer, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 9550
112. S. D. Walker, T. E. Barder, J. R. Martinelli, S. L. Buchwald, Angew. Chem. 2004, 116, 1907
113. Angew. Chem. Int. Ed. 2004, 43, 1871
114. R. Martin, S. L. Buchwald, J. Am. Chem. Soc. 2007, 129, 3844.
115. M. G. Organ, S. Avola, I. Dubovyk, N. Hadei, E. A. B. Kantchev, C. J. O'Brien, C. Valente, Chem. Eur. J. 2006, 12, 4749
116. M. G. Organ, M. Abdel-Hadi, S. Avola, N. Hadei, J. Nasielski, C. J. O'Brien, C. Valente, Chem. Eur. J. 2007, 13, 150
117. M. G. Organ, S. Calimsiz, M. Sayah, K. H. Hoi, A. J. Lough, Angew. Chem. 2009, 121, 2419
118. Angew. Chem. Int. Ed. 2009, 48, 2383.