Azobenzene-tethered bis(trityl alcohol) as a photoswitchable cooperative acid catalyst for Morita-Baylis-Hillman reactions

Chemistry - A European Journal

Volumn 18, Issue 35, 2012, Pages 10802-10807

  Imahori, Tatsushi ^a   Yamaguchi, Ryo ^a   Kurihara, Seiji ^a  

^a KUMAMOTO UNIVERSITY   (Japan)

Author keywords

acid catalysts; azo compounds; cooperative catalysts; Morita Baylis Hillman reaction; photochemistry

Indexed keywords

ACID CATALYST; AZO COMPOUND; LIGHT STIMULI; MORITA-BAYLIS-HILLMAN REACTION; PHOTO-SWITCHABLE; POSITIONAL RELATIONSHIP;

CATALYSTS; PHOTOCHEMICAL REACTIONS;

RATE CONSTANTS;

ALCOHOL DERIVATIVE; AZO COMPOUND; AZOBENZENE;

ARTICLE; CATALYSIS; CHEMISTRY; LIGHT; PHOTOCHEMISTRY; SPECTROSCOPY; STEREOISOMERISM;

ALCOHOLS; AZO COMPOUNDS; CATALYSIS; LIGHT; PHOTOCHEMICAL PROCESSES; SPECTRUM ANALYSIS; STEREOISOMERISM;

EID: 84865248696     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201201383     Document Type: Article

References (71)

1. Molecular Switches (Ed.:, B. L. Feringa,), Wiley-VCH, Weinheim, 2001
2. V. Balzani, M. Venturi, A. Credi, Molecular Devices and Machines, Wiley-VCH, Weinheim, 2008
3. E. R. Kay, D. A. Leigh, F. Zerbetto, Angew. Chem. 2007, 119, 72-196
4. Angew. Chem. Int. Ed. 2007, 46, 72-191
5. O. Sato, J. Tao, Y.-Z. Zhang, Angew. Chem. 2007, 119, 2200-2236
6. Angew. Chem. Int. Ed. 2007, 46, 2152-2187
7. A. P. R. Johnston, G. K. Such, F. Caruso, Angew. Chem. 2010, 122, 2723-2725
8. Angew. Chem. Int. Ed. 2010, 49, 2664-2666
9. Special Issue: "Photochromism", M. Irie, Chem. Rev. 2000, 100, 1683-1890
10. I. Willner, S. Rubin, Angew. Chem. 1996, 108, 419-439
11. Angew. Chem. Int. Ed. Engl. 1996, 35, 367-385
12. G. Mayer, A. Heckel, Angew. Chem. 2006, 118, 5020-5042
13. Angew. Chem. Int. Ed. 2006, 45, 4900-4921
14. P. Gorostiza, E. Y. Isacoff, Science 2008, 322, 395-399
15. K. Kinbara, T. Muraoka, T. Aida, Org. Biomol. Chem. 2008, 6, 1871-1876.
16. H. Maeda, Y. Bando, K. Shimomura, I. Yamada, M. Naito, K. Nobusawa, H. Tsumatori, T. Kawai, J. Am. Chem. Soc. 2011, 133, 9266-9269
17. J. Wang, L. Hou, W. R. Browne, B. L. Feringa, J. Am. Chem. Soc. 2011, 133, 8162-8164
18. E. Kim, D. Kim, H. Jung, J. Lee, S. Paul, N. Selvapalam, Y. Yang, N. Lim, C. G. Park, K. Kim, Angew. Chem. 2010, 122, 4507-4510
19. Angew. Chem. Int. Ed. 2010, 49, 4405-4408
20. H. J. Yoon, J. Kuwabara, J.-H. Kim, C. A. Mirkin, Science 2010, 330, 66-69
21. H. Komatsu, S. Matsumoto, S. Tamaru, K. Kaneko, M. Ikeda, I. Hamachi, J. Am. Chem. Soc. 2009, 131, 5580-5585
22. V. Blanco, A. Carlone, K. D. Hanni, D. A. Leigh, B. Lewandowski, Angew. Chem. 2012, 124, 5256-5259
23. Angew. Chem. Int. Ed. 2012, 51, 5166-5169.
24. R. S. Stoll, S. Hecht, Angew. Chem. 2010, 122, 5176-5200
25. Angew. Chem. Int. Ed. 2010, 49, 5054-5075.
26. V. N. Parmon, Catal. Today 1997, 39, 137-144
27. A. J. Esswein, D. G. Nocera, Chem. Rev. 2007, 107, 4022-4047
28. G. Palmisano, V. Augugliaro, M. Pagliaro, L. Palmisano, Chem. Commun. 2007, 3425-3437.
29. S. A. MacDonald, C. G. Willson, J. M. J. Fréchet, Acc. Chem. Res. 1994, 27, 151-158
30. D. Wang, K. Wurst, W. Knolle, U. Decker, L. Prager, S. Naumov, M. R. Buchmeiser, Angew. Chem. 2008, 120, 3311-3314
31. Angew. Chem. Int. Ed. 2008, 47, 3267-3270.
32. M. V. Peters, R. S. Stoll, A. Kühn, S. Hecht, Angew. Chem. 2008, 120, 6056-6060
33. Angew. Chem. Int. Ed. 2008, 47, 5968-5972
34. J. Wang, B. L. Feringa, Science 2011, 331, 1429-1432
35. O. B. Berryman, A. C. Sather, A. Lledo, J. Rebek, Jr., Angew. Chem. 2011, 123, 9572-9575
36. Angew. Chem. Int. Ed. 2011, 50, 9400-9403.
37. Bifunctional Molecular Catalysis, T. Ikariya, M. Shibasaki, Top. Organomet. Chem. 2011, 37, 1-210
38. P. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248-5286
39. Angew. Chem. Int. Ed. 2004, 43, 5138-5175
40. M. Shibasaki, M. Kanai, K.-I. Funabashi, Chem. Commun. 2002, 1989-1999
41. T. Ooi, M. Takahashi, M. Yamada, E. Tayama, K. Omoto, K. Maruoka, J. Am. Chem. Soc. 2004, 126, 1150-1160. Our recent reports on bifunctional cooperative catalyst systems, see
42. C. H. Cheon, T. Imahori, H. Yamamoto, Chem. Commun. 2010, 46, 6980-6982
43. T. Imahori, H. Ojima, Y. Yoshimura, H. Takahata, Chem. Eur. J. 2008, 14, 10762-10771.
44. F. Würthner, J. Rebek, Jr., Angew. Chem. 1995, 107, 503-505
45. Angew. Chem. Int. Ed. Engl. 1995, 34, 446-448
46. R. Cacciapaglia, S. Di Stefano, L. Mandolini, J. Am. Chem. Soc. 2003, 125, 2224-2227. Although details of the catalyst activity are unclear, an azobenzene-tethered bis-copper complex with a similar cooperative function mechanism has been reported for photoswitchable DNA cleavage, see
47. H. Prakash, A. Shodai, H. Yasui, H. Sakurai, S. Hirota, Inorg. Chem. 2008, 47, 5045-5047.
48. D. Sud, T. B. Norsten, N. R. Branda, Angew. Chem. 2005, 117, 2055-2057
49. Angew. Chem. Int. Ed. 2005, 44, 2019-2021.
50. A. Kausar, H. Nagano, Y. Kuwahara, T. Ogata, S. Kurihara, Chem. Eur. J. 2011, 17, 508-515
51. A. Kausar, H. Nagano, T. Ogata, T. Nonaka, S. Kurihara, Angew. Chem. 2009, 121, 2178-2181
52. Angew. Chem. Int. Ed. 2009, 48, 2144-2147
53. Md. Z. Alam, T. Yoshioka, T. Ogata, T. Nonaka, S. Kurihara, Chem. Eur. J. 2007, 13, 2641-2647
54. T. Yoshioka, T. Ogata, T. Nonaka, M. Moritsugu, S.-N. Kim, S. Kurihara, Ad. Mater. 2005, 17, 1226-1229.
55. A. K. Unni, N. Takenaka, H. Yamamoto, V. H. Rawal, J. Am. Chem. Soc. 2005, 127, 1336-1337.
56. H. Yamamoto, K. Futatsugi, Angew. Chem. 2005, 117, 1958-1977
57. Angew. Chem. Int. Ed. 2005 44 1924-1942.
58. P. Christ, A. G. Lindsay, S. S. Vormittag, J.-M. Neudörfl, A. Berkessel, A. C. O'Donogue, Chem. Eur. J. 2011, 17, 8524-8528.
59. T. Kawasaki, M. Tokuhiro, N. Kimizuka, T. Kunitake, J. Am. Chem. Soc. 2001, 123, 6792-6800.
60. Photochromism: Molecules and Systems (Eds.:, H. Dürr, H. Bouas-Laurent,), Elsevier, Amsterdam, 2003.
61. R. Irie, A. Tanoue, S. Urakawa, T. Imahori, K. Igawa, T. Matsumoto, K. Tomooka, S. Kikuta, T. Uchida, T. Katsuki, Chem. Lett. 2011, 40, 1343-1345
62. S. K. Collins, A. Grandbois, M. P. Vachon, J. CÁté, Angew. Chem. 2006, 118, 2989-2992
63. Angew. Chem. Int. Ed. 2006, 45, 2923-2926
64. Y. Kitahara, K. Tanaka, Chem. Commun. 2002, 932-933
65. H. Wynberg, M. B. Groen, H. Schadenberg, J. Org. Chem. 1971, 36, 2797-2809.
66. Y. M. A. Yamada, S. Ikegami, Tetrahedron Lett. 2000, 41, 2165-2169
67. N. T. McDougal, S. E. Schaus, J. Am. Chem. Soc. 2003, 125, 12094-12095.
68. A. N. Thadani, A. R. Stankovic, V. H. Rawal, Pros. Natl. Acad. Soc. 2004, 101, 5846-5850
69. Y. Huang, A. K. Unni, A. N. Thadani, V. H. Rawal, Nature 2003, 424, 146-146.
70. For the intramolecular hydrogen-bonding in a close derivative of 7, see;, K. A. Carey, W. Clegg, M. R. J. Elsegood, B. T. Golding, H. Maskill, Acta Crystallogr. E 2003, 59, o 263 -o 265.
71. F. Toda, A. Kai, R. Toyotaka, W.-H. Yip, T. C. W. Mak, Chem. Lett. 1989, 18, 1921-1924.