Abstract
Chlorinated phthalocyanine iron(II) complex is an excellent catalyst
for the oxidation of alkanes and alkenes with molecular oxygen in
the presence of acetaldehyde under O2 (1 atm) at room temperature.
The catalyst can be easily separated and reused for the next reaction.
Key words
oxidations - molecular oxygen - alkanes - iron
phthalocyanine catalyst
References
1
Murahashi S.-I.
Angew.
Chem., Int. Ed. Engl.
1995,
34:
2443
2a
Sheldon RA.
Kochi JK. In
Metal-Catalyzed Oxidations
of Organic Compounds
Academic Press;
New York:
1981.
2b
Barton DHR.
Doller D.
Acc.
Chem. Res.
1992,
25:
504
2c
Shilov AE.
Shul’pin G.
Chem
Rev.
1997,
97:
2879
3a
Murahashi S.-I.
Komiya N.
Oda Y.
Kuwabara T.
Naota T.
J. Org. Chem.
2000,
65:
9186
3b
Murahashi
S.-I.
Oda Y.
Naota T.
Kuwabara T.
Tetrahedron Lett.
1993,
34:
1299
3c
Murahashi S.-I.
Oda Y.
Komiya N.
Naota T.
Tetrahedron Lett.
1994,
35:
7953
4a
Murahashi S.-I.
Oda Y.
Naota T.
J. Am. Chem. Soc.
1992,
114:
7913
4b
Murahashi S.-I.
Oda Y.
Naota T.
Komiya N.
J. Chem, Soc., Chem. Commun.
1993,
139
4c
Komiya N.
Naota T.
Oda Y.
Murahashi S.-I.
J. Mol. Catal. A: Chem.
1997,
117:
21
5
Murahashi S.-I.
Saito T.
Naota T.
Kumobayashi H.
Akutagawa S.
Tetrahedron
Lett.
1991,
32:
5991
6
Murahashi S.-I.
Naota T.
Komiya N.
Tetrahedron
Lett.
1995,
36:
8059
7
Groves JT.
Bonchio M.
Carofiglio T.
Shalyaev K.
J. Am. Chem. Soc.
1996,
118:
8961
8a
Berezin BD. In
Coordination
Compounds of Porphyrins and Phthalocyanies
John
Wiley & Sons;
Chichester:
1981.
p.11-22
8b In
Metalloporphyrin Catalyzed Oxidations
Montanari
F., Casella L., Kluwer Academic;
Dordrecht:
1994.
9a
Bulkus KJ.
Eissa M.
Levado R.
J. Am. Chem.
Soc.
1995,
117:
10753
9b
Parton RF.
Peere GJ.
Neys PE.
Jacobs PA.
Claessens R.
Baron GV.
J.
Mol. Catal A: Chem.
1996,
113:
445
9c
Raja R.
Ratnasamy P.
Catal. Lett.
1997,
48:
1
10a
Herron N.
Stucky GD.
Tolman CA.
J. Chem. Soc., Chem.
Commun.
1986,
1521
10b
Ichikawa M.
Kimura T.
Fukuoka A.
Stud.
Surf. Sci. Catal.
1991,
60:
335
11
Parton RF.
Vankelecom IFJ.
Casselman MJA.
Bezoukhanova CP.
Uytterhoeven JB.
Jacobs PA.
Nature (London)
1994,
370:
541
12a
Armengol E.
Corma A.
Forne’s V.
Garci’a H.
Primo J.
Appl. Catal.
A.: General
1999,
181:
305
12b
Ernst S.
Selle M.
Micropor. Mesopor. Mater.
1999,
27:
355
13
Parton RF.
Neys PE.
Jacobs PA.
Sosa RC.
Rouxhet PG.
J. Catal.
1996,
164:
341
14
d’Alessandro N.
Liberatore L.
Tonucci L.
Morvillo A.
Bressan M.
New
J. Chem.
2001,
25:
1319
The complexes are commercially
available except 1 -Ru(III), 2 -Fe(II),
and 5 -Fe(II) complexes.
15a
1 -Ru(III),
see: Keen IM.
Malerbi BW.
J. Inorg. Nucl. Chem.
1965,
27:
1311
15b
2 -Fe(II),
see: Jones JG.
Twigg MV.
Inorg. Chem.
1969,
8:
2018
15c
5 -Fe(II),
see: Metz J.
Schneider O.
Hanack M.
Inorg. Chem.
1984,
23:
1065
16 If the amount of acetaldehyde was
increased, the conversion of cyclohexane went up; however, the selectivity
was decreased due to the formation of undesirable over-oxidation
products such as adipic acid, glutaric acid, and succinic acid.
[3a ]
17 Evaporation of dichloromethane under
vacuum (to ca. 2 mL), addition of diethyl ether (30 mL), and filtration
gave 3 -Fe(II) complex.
18a
Kasuga K.
Tsuboi K.
Handa M.
Sugimori T.
Sugebe K.
Inorg. Chem. Commun.
1999,
2:
507
18b
Nino ME.
Giraldo SA.
Pez-Mozo EA.
J. Mol. Catal. A: Chem.
2001,
175:
139
19
Khanna RK.
Pauling TM.
Vajpayee D.
Tetrahedron Lett.
1991,
32:
3759
20
Sakurai H.
Hosomi A.
J. Am. Chem. Soc.
1967,
89:
458
21
Sorokin A.
Robert A.
Meunier B.
J.
Am. Chem. Soc.
1993,
115:
7293
22
Ohkatsu Y.
Hara T.
Osa T.
Bull.
Chem. Soc. Jpn.
1977,
50:
692