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Abstract
Photocycloaddition of cyclohexenones with vinyl acetates or vinyl ethers, and the Paterno–Büchi reaction were carried out using photomicroreactors in combination with compact light sources such as low-power black lights and UV LEDs. The observed high efficiency holds promise as an energy-saving protocol for photoinduced [2 + 2] cycloaddition reactions.
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1. (a) Horpool, W.; Lenci, F., Eds. Handbook of Organic Photochemistry and Photobiology, 2nd ed.; CRC Press: Boca Raton, FL, 2004.
(b)Hoffmann, N. Chem. Rev. 2008, 108, 1052.
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2. For reviews on [2 + 2] photocycloaddition: (a) Bach, T. Synthesis 1998, 683.
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3. For reviews , see: (a) Ehrfeld, W.; Hessel, V.; Lowe, H. Microreactors: New Technology for Modern Chemistry; Wiley-VCH: Weinheim, 2000.
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4. For our review, see: Fukuyama, T.; Rahman, M. T.; Sato, M.; Ryu, I. Synlett 2008, 151.
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5. Our recent work using a microreactor, see: (a) Fukuyama, T.; Shinmen, M.; Nishitani, S.; Sato, M.; Ryu, I. Org. Lett. 2002, 4, 1691.
(b)Liu, S.; Fukuyama, T.; Sato, M.; Ryu, I. Org. Process Res. Dev. 2004, 8, 477.
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(d)Fukuyama, T.; Kobayashi, M.; Rahman, M. T.; Ryu, I. Org. Lett. 2008, 10, 533.
(e)Wienhöfer, I. C.; Studer, A.; Rahman, M. T.; Fukuyama, T.; Ryu, I. Org. Lett. 2009, 11, 2457.
(f)Fukuyama, T.; Rahman, M. T.; Kamata, N.; Ryu, I. Beilstein J. Org. Chem. 2009, 5, 34.
(g)Sugimoto, A.; Fukuyama, T.; Rahman, M. T.; Ryu, I. Tetrahedron Lett. 2009, 50, 6364.
(h)Fukuyama, T.; Kippo, T.; Ryu, I.; Sagae, T. Res. Chem. Intermediate 2009, 35, 1053.
(i)Min, K.-I.; Lee, T.-H.; Park, C. P.; Wu, Z.-Y.; Girault, H. H.; Ryu, I.; Fukuyama, T.; Mukai, Y.; Kim, D.-P. Angew. Chem. Int. Ed. 2010, 49, 7063.
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6. Examples of photoreactions using a microreactor, (a) Lu, H.; Schmidt, M. A.; Jensen, K. F. Lab Chip 2001, 1, 22.
(b)Ueno, K.; Kitagawa, F.; Kitamura, N. Lab Chip. 2002, 2, 231.
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(o)Hook, B. D. A.; Dohle, W.; Hirst, P. R.; Pickworth, M.; Berry, M. B.; Booker-Milburn, K. I. J. Org. Chem. 2005, 70, 7558.
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7. Reviews on photoreactions using a microreactor, see: (a) Matsushita, Y.; Ichimura, T.; Ohba, N.; Kumada, S.; Sakeda, K.; Suzuki, T.; Tanibata, H.; Murata, T. Pure Appl. Chem. 2007, 79, 1959.
(b)Coyle, E. E.; Oelgemöller, M. Photochem. Photobiol. Sci. 2008, 7, 1313.
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8. For our preliminary report on photo-induced [2 + 2] cycloaddition in a microflow system: (a) Fukuyama, T.; Hino, Y.; Kamata, N.; Ryu, I. Chem. Lett. 2004, 33, 1430. Also see:
(b)Tsutsumi, K.; Terao, K.; Yamaguchi, H.; Yoshimura, S.; Morimoto, T.; Kakiuchi, K.; Fukuyama, T.; Ryu, I. Chem. Lett. 2010, 39, 828.
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9. (a) Sugimoto, A.; Takagi, M.; Sumino, Y.; Fukuyama, T.; Ryu, I. Tetrahedron Lett. 2006, 47, 6197.
(b)Sugimoto, A.; Fukuyama, T.; Sumino, Y.; Takagi, M.; Ryu, I; Tetrahedron 2009, 65, 1593.
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10. Matsubara, H.; Hino, Y.; Tokizane, M.; Ryu, I. Chem. Eng. J. 2011, 167, 567.
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11. For earlier work on photochemical [2 + 2] cycloadditon of cyclohexenones with vinyl acetates: (a) Corey, E. J.; Bass, J. D.; LeMahieu, R.; Mitra, R. B. J. Am. Chem. Soc. 1964, 86, 5570.
(b)Hunter, N. R.; MacAlpine, G. A.; Liu, H. J.; Valenta, Z. Can. J. Chem. 1970, 48, 1436.
(c)Liu, H.-J.; Yao, P. C.-L. Can. J. Chem. 1977, 55, 822.
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12. For a review on Paterno-Büchi reaction: Porco, J. A., Jr.; Shreiber S. L. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pargamon: Oxford, 1991; Vol. 5, pp 151–192.
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13. Adam, W.; Stegmann, V. R. Synthesis 2001, 1203.
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14. The transmission of Foturan® glass is approximately 30% at 300 nm. For details, see: http://www.mikroglas.com/index.php?PAGE_ID=509#.
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15. For details , see: http://www.keyboardchemistry.com/en/custom.html.
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| Journal of Flow Chemistry | |
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