Practical synthesis of photochromic diarylethenes in integrated flow microreactor systems

ChemSusChem

Volumn 5, Issue 2, 2012, Pages 339-350

  Asai, Tatsuro ^a   Takata, Atsushi ^b   Nagaki, Aiichiro ^a   Yoshida, Jun Ichi ^a  

^a KYOTO UNIVERSITY   (Japan)

^b Yamada Chemical Co Ltd   (Japan)

Author keywords

diarylethenes; microreactors; organometallic compounds; photochromism

Indexed keywords

CHEMICAL REACTORS; CHEMICALS; CRYOGENICS; OLEFINS; ORGANOMETALLICS; PHOTOCHROMISM; STEEL BEAMS AND GIRDERS;

ARYL GROUP; BATCH SYSTEMS; CRYOGENIC CONDITIONS; DIARYLETHENE DERIVATIVES; DIARYLETHENES; EFFECTIVE TEMPERATURE; HETEROARYLLITHIUMS; LABORATORY SCALE; MACROSYSTEMS; MICRO REACTOR; MICROREACTOR SYSTEM; ORGANOMETALLIC COMPOUNDS; PHOTOCHROMIC DIARYLETHENES; RESIDENCE TIME;

INTEGRATION;

ALKENE; CYCLOPENTANE DERIVATIVE; LITHIUM;

ARTICLE; CHEMISTRY; METHODOLOGY; MICROTECHNOLOGY; PHOTOCHEMISTRY; SYNTHESIS; SYSTEM ANALYSIS;

ALKENES; CHEMISTRY TECHNIQUES, SYNTHETIC; CYCLOPENTANES; LITHIUM; MICROTECHNOLOGY; PHOTOCHEMICAL PROCESSES; SYSTEMS INTEGRATION;

EID: 84858690217     PISSN: 18645631     EISSN: 1864564X     Source Type: Journal    
DOI: 10.1002/cssc.201100376     Document Type: Article

References (121)

1. A. Toriumi, S. Kawata, M. Gu, Opt. Lett. 1998, 23, 1924
2. S. L. Gilat, S. H. Kawai, J.-M. Lehn, Chem. Eur. J. 1995, 1, 275
3. M. Irie, K. Uchida, Bull. Chem. Soc. Jpn. 1998, 71, 985
4. M. Irie, Chem. Rev. 2000, 100, 1685
5. K. Matsuda, M. Irie, J. Am. Chem. Soc. 2001, 123, 9896
6. M. Irie, T. Fukaminato, T. Sasaki, N. Tamai, T. Kawai, Nature 2002, 420, 759
7. T. Kawai, Y. Nakashima, M. Irie, Adv. Mater. 2005, 17, 309.
8. G. Berkovic, V. Krongauz, V. Weiss, Chem. Rev. 2000, 100, 1741
9. S. Kawata, Y. Kawata, Chem. Rev. 2000, 100, 1777
10. B. L. Feringa, R. A. van Delden, N. Koumura, E. M. Geerts, Chem. Rev. 2000, 100, 1789
11. H. Bouas-Laurent, H. Dürr, Pure Appl. Chem. 2001, 73, 639
12. F. M. Raymo, M. Tamosulo, Chem. Soc. Rev. 2005, 34, 327.
13. L. N. Lucas, J. J. D. de Jong, J. H. van Esch, R. M. Kellogg, B. L. Feringa, Eur. J. Org. Chem. 2003, 155
14. M. Morimoto, S. Kobatake, M. Irie, J. Am. Chem. Soc. 2003, 125, 11080
15. J. J. D. de Jong, L. N. Lucas, R. Hania, A. Pugzlys, R. M. Kellogg, B. L. Feringa, K. Duppen, J. H. van Esch, Eur. J. Org. Chem. 2003, 1887
16. J. J. D. de Jong, L. N. Lucas, R. M. Kellogg, J. H. van Esch, B. L. Feringa, Science 2004, 304, 278
17. H. Choi, H. Lee, Y. Kang, E. Kim, S. O. Kang, J. Ko, J. Org. Chem. 2005, 70, 8291
18. K. Higashiguchi, K. Matsuda, N. Tanifuji, M. Irie, J. Am. Chem. Soc. 2005, 127, 8922.
19. K. Uchida, K. Nakayama, M. Irie, Bull. Chem. Soc. Jpn. 1990, 63 1311
20. M. Hanazawa, R. Sumiya, Y. Horikawa, M. Irie, J. Chem. Soc. Chem. Commun. 1992, 206
21. K. Uchida, T. Ishikawa, M. Takeshita, M. Irie, Tetrahedron 1998, 54, 6627
22. T. Yamaguchi, M. Irie, J. Org. Chem. 2005, 70, 10323.
23. J. Clayden, Organolithiums: Selectivity for Synthesis, Pergamon, Amsterdam, 2002
24. Z. Rappoport, I. Marek, The Chemistry of Organolithium Compounds, Wiley, Chichester, 2004.
25. W. Ehrfeld, V. Hessel, H. Löwe, Microreactors, Wiley-VCH, Weinheim, 2000
26. V. Hessel, S. Hardt, H. Löwe, Chemical Micro Process Engineering, Wiley-VCH, Weinheim, 2004
27. J. Yoshida, Flash Chemistry. Fast Organic Synthesis in Microsystems, Wiley, Chichester, 2008
28. V. Hessel, A. Renken, J. C. Schouten, J. Yoshida, Micro Process Engineering, Wiley-VCH, Weinheim, 2009.
29. K. Jähnisch, V. Hessel, H. Löwe, M. Baerns, Angew. Chem. 2004, 116, 410
30. Angew. Chem. Int. Ed. 2004, 43, 406
31. G. N. Doku, W. Verboom, D. N. Reinhoudt, A. van den Berg, Tetrahedron 2005, 61, 2733
32. J. Yoshida, A. Nagaki, T. Iwasaki, S. Suga, Chem. Eng. Technol. 2005, 28, 259
33. P. Watts, S. J. Haswell, Chem. Soc. Rev. 2005, 34, 235
34. K. Geyer, J. D. C. Codee, P. H. Seeberger, Chem. Eur. J. 2006, 12, 8434
35. A. J. deMello, Nature 2006, 442, 394
36. H. Song, D. L. Chen, R. F. Ismagilov, Angew. Chem. 2006, 118, 7494
37. Angew. Chem. Int. Ed. 2006, 45, 7336
38. J. Kobayashi, Y. Mori, S. Kobayashi, Chem. Asian J. 2006, 1, 22
39. M. Brivio, W. Verboom, D. N. Reinhoudt, Lab Chip 2006, 6, 329
40. B. P. Mason, K. E. Price, J. L. Steinbacher, A. R. Bogdan, D. T. McQuade, Chem. Rev. 2007, 107, 2300
41. B. Ahmed-Omer, J. C. Brandtand, T. Wirth, Org. Biomol. Chem. 2007, 5, 733
42. P. Watts, C. Wiles, Chem. Commun. 2007, 443
43. T. Fukuyama, M. T. Rahman, M. Sato, I. Ryu, Synlett 2008, 151
44. J. Yoshida, A. Nagaki, T. Yamada, Chem. Eur. J. 2008, 14, 7450
45. R. L. Hartman, K. F. Jensen, Lab Chip 2009, 9, 2495
46. J. Yoshida, Chem. Rec. 2010, 10, 332
47. J. Yoshida, H. Kim, A. Nagaki, ChemSusChem 2011, 4, 331
48. J. Yoshida, K. Saito, T. Nokami, A. Nagaki, Synlett 2011, 1189.
49. S. Suga, M. Okajima, K. Fujiwara, J. Yoshida, J. Am. Chem. Soc. 2001, 123, 7941
50. C. Wiles, P. Watts, S. J. Haswell, E. Pombo-Villar, Chem. Commun. 2002, 1034
51. T. Fukuyama, M. Shinmen, S. Nishitani, M. Sato, I. Ryu, Org. Lett. 2002, 4, 1691
52. M. Ueno, H. Hisamoto, T. Kitamori, S. Kobayashi, Chem. Commun. 2003, 936
53. K. Mikami, M. Yamanaka, M. N. Islam, K. Kudo, N. Seino, M. Shinoda, Tetrahedron Lett. 2003, 44, 7545
54. J. Kobayashi, Y. Mori, K. Okamoto, R. Akiyama, M. Ueno, T. Kitamori, S. Kobayashi, Science 2004, 304, 1305
55. A. Nagaki, K. Kawamura, S. Suga, T. Ando, M. Sawamoto, J. Yoshida, J. Am. Chem. Soc. 2004, 126, 14702
56. A. Nagaki, M. Togai, S. Suga, N. Aoki, K. Mae, J. Yoshida, J. Am. Chem. Soc. 2005, 127, 11666
57. T. Kawaguchi, H. Miyata, K. Ataka, K. Mae, J. Yoshida, Angew. Chem. 2005, 117, 2465
58. Angew. Chem. Int. Ed. 2005, 44, 2413
59. P. He, P. Watts, F. Marken, S. J. Haswell, Angew. Chem. 2006, 118, 4252
60. Angew. Chem. Int. Ed. 2006, 45, 4146
61. T. Hatakeyama, D. L. Chen, R. F. Ismagilov, J. Am. Chem. Soc. 2006, 128, 2518
62. Y. Uozumi, Y. Yamada, T. Beppu, N. Fukuyama, M. Ueno, T. Kitamori, J. Am. Chem. Soc. 2006, 128, 15994
63. K. Tanaka, S. Motomatsu, K. Koyama, S. Tanaka, K. Fukase, Org. Lett. 2007, 9, 299
64. H. R. Sahoo, J. G. Kralj, K. F. Jensen, Angew. Chem. 2007, 119, 5806
65. Angew. Chem. Int. Ed. 2007, 46, 5704
66. C. H. Hornung, M. R. Mackley, I. R. Baxendale, S. V. Ley, Org. Process Res. Dev. 2007, 11, 399
67. T. Fukuyama, M. Kobayashi, M. T. Rahman, N. Kamata, I. Ryu, Org. Lett. 2008, 10, 533
68. K. Tanaka, T. Miyagawa, K. Fukase, Synlett 2009, 1571
69. A. Nagaki, E. Takizawa, J. Yoshida, Chem. Lett. 2009, 38, 486
70. A. Nagaki, E. Takizawa, J. Yoshida, Chem. Lett. 2009, 38, 1060
71. I. C. Wienhöfer, A. Studer, M. T. Rahman, T. Fukuyama, I. Ryu, Org. Lett. 2009, 11, 2457
72. A. R. Bogdan, S. L. Poe, D. C. Kubis, S. J. Broadwater, D. T. McQuade, Angew. Chem. 2009, 121, 8699
73. Angew. Chem. Int. Ed. 2009, 48, 8547
74. Y. Matsushita, M. Iwasawa, T. Suzuki, T. Ichimura, Chem. Lett. 2009, 38, 846
75. T. Oishi, T. Imaizumi, M. Murata, Chem. Lett. 2010, 39, 108
76. K. Tsutsumi, K. Terao, H. Yamaguchi, S. Yoshimura, T. Morimoto, K. Kakiuchi, T. Fukuyama, I. Ryu, Chem. Lett. 2010, 39, 828
77. S. Fuse, N. Tanabe, M. Yoshida, H. Yoshida, T. Doi, T. Takahashi, Chem. Commun. 2010, 46, 8722.
78. S. Suga, D. Yamada, J. Yoshida, Chem. Lett. 2010, 39, 404
79. A. Nagaki, A. Kenmoku, Y. Moriwaki, A. Hayashi, J. Yoshida, Angew. Chem. 2010, 122, 7705
80. Angew. Chem. Int. Ed. 2010, 49, 7543.
81. A. Nagaki, Y. Tomida, H. Usutani, H. Kim, N. Takabayashi, T. Nokami, H. Okamoto, J. Yoshida, Chem. Asian J. 2007, 2, 1513
82. H. Usutani, Y. Tomida, A. Nagaki, H. Okamoto, T. Nokami, J. Yoshida, J. Am. Chem. Soc. 2007, 129, 3046
83. A. Nagaki, E. Takizawa, J. Yoshida, J. Am. Chem. Soc. 2009, 131, 1654
84. Y. Tomida, A. Nagaki, J. Yoshida, Org. Lett. 2009, 11, 3614
85. A. Nagaki, H. Kim, J. Yoshida, Angew. Chem. 2009, 121, 8207
86. Angew. Chem. Int. Ed. 2009, 48, 8063
87. A. Nagaki, E. Takizawa, J. Yoshida, Chem. Eur. J. 2010, 16, 14149
88. A. Nagaki, H. Kim, Y. Moriwaki, C. Matsuo, J. Yoshida, Chem. Eur. J. 2010, 16, 11167
89. A. Nagaki, H. Kim, H. Usutani, C. Matsuo, J. Yoshida, Org. Biomol. Chem. 2010, 8, 1212
90. Y. Tomida, A. Nagaki, J. Yoshida, J. Am. Chem. Soc. 2011, 133, 3744
91. H. Kim, A. Nagaki, J. Yoshida, Nat. Commun. 2011, 2, 264
92. A. Nagaki, S. Yamada, M. Doi, Y. Tomida, N. Takabayashi, J. Yoshida, Green Chem. 2011, 13, 1110.
93. Y. Ushiogi, T. Hase, Y. Iinuma, A. Takata, J. Yoshida, Chem. Commun. 2007, 2947.
94. T. Asai, A. Takata, Y. Ushiogi, Y. Iinuma, A. Nagaki, Y. Yoshida, Chem. Lett. 2011, 40, 393.
95. M. Irie, T. Lifka, K. Uchida, S. Kobatake, Y. Shindo, Chem. Commun. 1999, 747
96. M. Irie, T. Lifka, S. Kobatake, N. Kato, J. Am. Chem. Soc. 2000, 122, 4871
97. S. Kobatake, K. Uchida, E. Tsuchida, M. Irie, Chem. Lett. 2000, 1340.
98. T. Schwalbe, V. Autze, M. Hohmann, W. Stirner, Org. Process Res. Dev. 2004, 8, 440
99. X. Zhang, S. Stefanick, F. J. Villani, Org. Process Res. Dev. 2004, 8, 455
100. H. Pennemann, V. Hessel, H. Löwe, Chem. Eng. Sci. 2004, 59, 4789
101. D. M. Ratner, E. R. Murphy, M. Jhunjhunwala, D. A. Snyder, K. F. Jensen, P. H. Seeberger, Chem. Commun. 2005, 578
102. O. Flögel, J. D. C. Codee, D. Seebach, P. H. Seeberger, Angew. Chem. 2006, 118, 7157
103. Angew. Chem. Int. Ed. 2006, 45, 7000
104. F. R. Carrel, K. Geyer, D. C. Jeroen, J. D. C. Codee, P. H. Seeberger, Org. Lett. 2007, 9, 2285
105. A. Nagaki, Y. Tomida, J. Yoshida, Macromolecules 2008, 41, 6322
106. A. Nagaki, Y. Tomida, A. Miyazaki, J. Yoshida, Macromolecules 2009, 42, 4384.
107. M. Irie, K. Sakemura, M. Okinaka, K. Uchida, J. Org. Chem. 1995, 60, 8305.
108. T. E. Barman, S. R. W. Bellamy, H. Gutfreund, S. E. Halford, C. Lionne, Cell. Mol. Life Sci. 2006, 63, 2571
109. W. P. Bula, W. Verboom, D. N. Reinhoudt, J. G. E. Gardeniers, Lab Chip 2007, 7, 1717.
110. K. Uchida, T. Ishikawa, M. Takeshita, M. Irie, Tetrahedron 1998, 54, 6627
111. S. Takami, T. Kawai, M. Irie, Eur. J. Org. Chem. 2002, 3796
112. L. Kuroki, S. Takami, K. Shibata, M. Irie, Chem. Commun. 2005, 6005.
113. K. Uchida, T. Ishikawa, M. Takeshita, M. Irie, Tetrahedron 1998, 54, 6627.
114. E. Kim, Y. Choi, M. Lee, Macromolecules 1999, 32, 4855.
115. T. Yamaguchi, M. Irie, Eur. J. Org. Chem. 2006, 3105.
116. S. Suga, A. Nagaki, J. Yoshida, Chem. Commun. 2003, 354
117. A. Nagaki, N. Takabayashi, Y. Tomida, J. Yoshida, Org. Lett. 2008, 10, 3937
118. A. Nagaki, N. Takabayashi, Y. Tomida, J. Yoshida, Beilstein J. Org. Chem. 2009, 5, 16.
119. P. Rys, Acc. Chem. Res. 1976, 9, 345
120. P. Rys, Angew. Chem. 1977, 89, 847
121. Angew. Chem. Int. Ed. Engl. 1977, 16, 807.