LETTER
Chlorinated Phthalocyanine Iron(II) Complex
323
Table 2 Oxidation of Hydrocarbons with O2 with 3-Fe(II) Catalysta
Substrates
Yield (%)b
Product (Selectivity /%)
TON
88
22
(50)
(50)
(50)c
OH
O
21c
80c
(50)c
47
188
OH
OH
O
(83)
(8)
(8)
6
22
(33)
(33)
(16)
OH
OH
O
O
(16)
OH
95
76
377
320
O
(56)
(44)
OH
(70)
O
(30)
O
a In a typical experiment, a mixture of substrate (40 mmol), 3-Fe(II) (0.010 mmol), acetaldehyde (4.0 mmol), and dry dichloromethane (10 mL)
was vigorously stirred at room temperature under oxygen atmosphere (1 atm). After the usual work up, the reaction mixture was analyzed by
GC and GC-MS.
b Yields were determined by GC analyses based on acetaldehyde used.
c The values were obtained by the reaction using the recycled catalyst.
(6) Murahashi, S.-I.; Naota, T.; Komiya, N. Tetrahedron Lett.
Acknowledgment
1995, 36, 8059.
This work was supported by the Research for the Future Program,
the Japan Society for the Promotion of Science.
(7) Groves, J. T.; Bonchio, M.; Carofiglio, T.; Shalyaev, K. J.
Am. Chem. Soc. 1996, 118, 8961.
(8) (a) Berezin, B. D. In Coordination Compounds of
Porphyrins and Phthalocyanies; John Wiley & Sons:
Chichester, 1981, 11–22. (b) In MetalloporphyrinCatalyzed
References
Oxidations; Montanari F., Casella L., Kluwer Academic:
Dordrecht, 1994.
(1) Murahashi, S.-I. Angew. Chem., Int. Ed. Engl. 1995, 34,
2443.
(9) (a) Bulkus, K. J. Jr.; Eissa, M.; Levado, R. J. Am. Chem. Soc.
1995, 117, 10753. (b) Parton, R. F.; Peere, G. J.; Neys, P. E.;
Jacobs, P. A.; Claessens, R.; Baron, G. V. J. Mol. Catal A:
Chem. 1996, 113, 445. (c) Raja, R.; Ratnasamy, P. Catal.
Lett. 1997, 48, 1.
(2) (a) Sheldon, R. A.; Kochi, J. K. In Metal-Catalyzed
Oxidations of Organic Compounds; Academic Press: New
York, 1981. (b) Barton, D. H. R.; Doller, D. Acc. Chem. Res.
1992, 25, 504. (c) Shilov, A. E.; Shul’pin, G. Chem Rev.
1997, 97, 2879.
(10) (a) Herron, N.; Stucky, G. D.; Tolman, C. A. J. Chem. Soc.,
Chem. Commun. 1986, 1521. (b) Ichikawa, M.; Kimura, T.;
Fukuoka, A. Stud. Surf. Sci. Catal. 1991, 60, 335.
(11) Parton, R. F.; Vankelecom, I. F. J.; Casselman, M. J. A.;
Bezoukhanova, C. P.; Uytterhoeven, J. B.; Jacobs, P. A.
Nature (London) 1994, 370, 541.
(12) (a) Armengol, E.; Corma, A.; Forne’s, V.; Garci’a, H.;
Primo, J. Appl. Catal. A.: General 1999, 181, 305.
(b) Ernst, S.; Selle, M. Micropor. Mesopor. Mater. 1999, 27,
355.
(3) (a) Murahashi, S.-I.; Komiya, N.; Oda, Y.; Kuwabara, T.;
Naota, T. J. Org. Chem. 2000, 65, 9186. (b) Murahashi,
S.-I.; Oda, Y.; Naota, T.; Kuwabara, T. Tetrahedron Lett.
1993, 34, 1299. (c) Murahashi, S.-I.; Oda, Y.; Komiya, N.;
Naota, T. Tetrahedron Lett. 1994, 35, 7953.
(4) (a) Murahashi, S.-I.; Oda, Y.; Naota, T. J. Am. Chem. Soc.
1992, 114, 7913. (b) Murahashi, S.-I.; Oda, Y.; Naota, T.;
Komiya, N. J. Chem, Soc., Chem. Commun. 1993, 139.
(c) Komiya, N.; Naota, T.; Oda, Y.; Murahashi, S.-I. J. Mol.
Catal. A: Chem. 1997, 117, 21.
(13) Parton, R. F.; Neys, P. E.; Jacobs, P. A.; Sosa, R. C.;
Rouxhet, P. G. J. Catal. 1996, 164, 341.
(14) d’Alessandro, N.; Liberatore, L.; Tonucci, L.; Morvillo, A.;
Bressan, M. New J. Chem. 2001, 25, 1319.
(5) Murahashi, S.-I.; Saito, T.; Naota, T.; Kumobayashi, H.;
Akutagawa, S. Tetrahedron Lett. 1991, 32, 5991.
Synlett 2003, No. 3, 321–324 ISSN 0936-5214 © Thieme Stuttgart · New York