Oxidative photodecarboxylation of α-hydroxycarboxylic acids and phenylacetic acid derivatives with FSM-16

Organic Letters

Volumn 2, Issue 3, 2000, Pages 331-333

  Itoh, Akichika ^a   Kodama, Tomohiro ^a   Inagaki, Shinji ^b   Masaki, Yukio ^a  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

^b Rd Management Section   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000279137     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991284z     Document Type: Article

References (33)

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20. Kim, Y. I.; Kim, Y. H. Tetrahedron Lett. 1998, 39, 639. Mohri, K.; Mamiya, J.; Kasahara, Y.; Isobe, K.; Tsuda, Y. Chem. Pharm. Bull. 1996, 44, 2218. Komuro, M.; Nagatsu, Y.; Higuchi, T.; Hirobe, M. Tetrahedron Lett. 1992, 33, 4949. Banerjee, A.; Hazra, B.; Bhattacharya, A.; Banerjee, S.; Banerjee, G. C.; Sengupta, S. Synthesis 1989, 765. Fristad, W. E.; Klang, J. A. Tetrahedron Lett. 1983, 24, 2219. Giordano, C.; Belli, A.; Citterio, A.; Minisci, F. J. Chem. Soc., Perkin Trans. 1 1981, 1574. Santaniello, E.; Ponti, F.; Manzocchi, A. Tetrahedron Lett. 1980, 21, 2655. Dessau, R. M.; Heiba, E. I. J. Org. Chem. 1975, 25, 3647.
21. Kim, Y. I.; Kim, Y. H. Tetrahedron Lett. 1998, 39, 639. Mohri, K.; Mamiya, J.; Kasahara, Y.; Isobe, K.; Tsuda, Y. Chem. Pharm. Bull. 1996, 44, 2218. Komuro, M.; Nagatsu, Y.; Higuchi, T.; Hirobe, M. Tetrahedron Lett. 1992, 33, 4949. Banerjee, A.; Hazra, B.; Bhattacharya, A.; Banerjee, S.; Banerjee, G. C.; Sengupta, S. Synthesis 1989, 765. Fristad, W. E.; Klang, J. A. Tetrahedron Lett. 1983, 24, 2219. Giordano, C.; Belli, A.; Citterio, A.; Minisci, F. J. Chem. Soc., Perkin Trans. 1 1981, 1574. Santaniello, E.; Ponti, F.; Manzocchi, A. Tetrahedron Lett. 1980, 21, 2655. Dessau, R. M.; Heiba, E. I. J. Org. Chem. 1975, 25, 3647.
22. Kim, Y. I.; Kim, Y. H. Tetrahedron Lett. 1998, 39, 639. Mohri, K.; Mamiya, J.; Kasahara, Y.; Isobe, K.; Tsuda, Y. Chem. Pharm. Bull. 1996, 44, 2218. Komuro, M.; Nagatsu, Y.; Higuchi, T.; Hirobe, M. Tetrahedron Lett. 1992, 33, 4949. Banerjee, A.; Hazra, B.; Bhattacharya, A.; Banerjee, S.; Banerjee, G. C.; Sengupta, S. Synthesis 1989, 765. Fristad, W. E.; Klang, J. A. Tetrahedron Lett. 1983, 24, 2219. Giordano, C.; Belli, A.; Citterio, A.; Minisci, F. J. Chem. Soc., Perkin Trans. 1 1981, 1574. Santaniello, E.; Ponti, F.; Manzocchi, A. Tetrahedron Lett. 1980, 21, 2655. Dessau, R. M.; Heiba, E. I. J. Org. Chem. 1975, 25, 3647.
23. Kim, Y. I.; Kim, Y. H. Tetrahedron Lett. 1998, 39, 639. Mohri, K.; Mamiya, J.; Kasahara, Y.; Isobe, K.; Tsuda, Y. Chem. Pharm. Bull. 1996, 44, 2218. Komuro, M.; Nagatsu, Y.; Higuchi, T.; Hirobe, M. Tetrahedron Lett. 1992, 33, 4949. Banerjee, A.; Hazra, B.; Bhattacharya, A.; Banerjee, S.; Banerjee, G. C.; Sengupta, S. Synthesis 1989, 765. Fristad, W. E.; Klang, J. A. Tetrahedron Lett. 1983, 24, 2219. Giordano, C.; Belli, A.; Citterio, A.; Minisci, F. J. Chem. Soc., Perkin Trans. 1 1981, 1574. Santaniello, E.; Ponti, F.; Manzocchi, A. Tetrahedron Lett. 1980, 21, 2655. Dessau, R. M.; Heiba, E. I. J. Org. Chem. 1975, 25, 3647.
24. Kim, Y. I.; Kim, Y. H. Tetrahedron Lett. 1998, 39, 639. Mohri, K.; Mamiya, J.; Kasahara, Y.; Isobe, K.; Tsuda, Y. Chem. Pharm. Bull. 1996, 44, 2218. Komuro, M.; Nagatsu, Y.; Higuchi, T.; Hirobe, M. Tetrahedron Lett. 1992, 33, 4949. Banerjee, A.; Hazra, B.; Bhattacharya, A.; Banerjee, S.; Banerjee, G. C.; Sengupta, S. Synthesis 1989, 765. Fristad, W. E.; Klang, J. A. Tetrahedron Lett. 1983, 24, 2219. Giordano, C.; Belli, A.; Citterio, A.; Minisci, F. J. Chem. Soc., Perkin Trans. 1 1981, 1574. Santaniello, E.; Ponti, F.; Manzocchi, A. Tetrahedron Lett. 1980, 21, 2655. Dessau, R. M.; Heiba, E. I. J. Org. Chem. 1975, 25, 3647.
25. Kim, Y. I.; Kim, Y. H. Tetrahedron Lett. 1998, 39, 639. Mohri, K.; Mamiya, J.; Kasahara, Y.; Isobe, K.; Tsuda, Y. Chem. Pharm. Bull. 1996, 44, 2218. Komuro, M.; Nagatsu, Y.; Higuchi, T.; Hirobe, M. Tetrahedron Lett. 1992, 33, 4949. Banerjee, A.; Hazra, B.; Bhattacharya, A.; Banerjee, S.; Banerjee, G. C.; Sengupta, S. Synthesis 1989, 765. Fristad, W. E.; Klang, J. A. Tetrahedron Lett. 1983, 24, 2219. Giordano, C.; Belli, A.; Citterio, A.; Minisci, F. J. Chem. Soc., Perkin Trans. 1 1981, 1574. Santaniello, E.; Ponti, F.; Manzocchi, A. Tetrahedron Lett. 1980, 21, 2655. Dessau, R. M.; Heiba, E. I. J. Org. Chem. 1975, 25, 3647.
26. Kim, Y. I.; Kim, Y. H. Tetrahedron Lett. 1998, 39, 639. Mohri, K.; Mamiya, J.; Kasahara, Y.; Isobe, K.; Tsuda, Y. Chem. Pharm. Bull. 1996, 44, 2218. Komuro, M.; Nagatsu, Y.; Higuchi, T.; Hirobe, M. Tetrahedron Lett. 1992, 33, 4949. Banerjee, A.; Hazra, B.; Bhattacharya, A.; Banerjee, S.; Banerjee, G. C.; Sengupta, S. Synthesis 1989, 765. Fristad, W. E.; Klang, J. A. Tetrahedron Lett. 1983, 24, 2219. Giordano, C.; Belli, A.; Citterio, A.; Minisci, F. J. Chem. Soc., Perkin Trans. 1 1981, 1574. Santaniello, E.; Ponti, F.; Manzocchi, A. Tetrahedron Lett. 1980, 21, 2655. Dessau, R. M.; Heiba, E. I. J. Org. Chem. 1975, 25, 3647.
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29. 2/g.
30. A typical procedure follows: Irradiation of a suspension of benzilic acid (1, 50 mg) and FSM-16 (100 mg) in dry hexane (5 mL) at room temperature with a 400-W high-pressure mercury lamp for 5 h. FSM-16 was then filtered off and washed with ethyl acetate, and the filtrate was concentrated under reduced pressure. Pure benzophenone (2) (35 mg, 88%) was obtained after purification by preparative TLC.
31. 2 in hexane is higher than that of other typical organic solvents, see: Che, Y.; Tokuda, K.; Ohsaka, T. Bull. Chem. Soc. Jpn. 1998, 71, 651.
32. The conversions using the additives except FSM-16 were not optimized.
33. The detected products of this reaction were 6 (8%) and 7 (2%). The yield was estimated on the ratio of integral value of 400 MHz NMR analysis.