Abstract
Metallodeuteroporphyrins with two side chains linked by a terminal cystine dimethyl ester [M(PDTEP), where M = ClFe(III), ClMn(III), Co(II)], have been synthesised. These metalloporpyirn complexes were found to act as efficient catalysts in the oxidation of cyclohexane to cyclohexanol and cyclohexanone using air as the oxygen source and in the absence of additives and solvents. The influence of the central metal, reaction temperature and pressure on the catalytic behavior of M(PDTEP) were evaluated. The high conversion and selectivity of M(PDTEP) was ascribed to the existence of intramolecular coordination by the M(PDTEP).
References
1.
Meunier B.
,
Visser S.P.
, and
Shaik S.
, Chem. Rev. , 2004 , 104 , 3947 .
2.
Rezaeifard A.
,
Jafarpour M.
,
Moghaddam G.K.
, and
Amini F.
, Bioorg. Med. Chem. , 2007 , 15 , 3097 .
3.
Che C.M.
,
Lo V.K.Y.
,
Zhou C.Y.
, and
Huang J.S.
, Chem. Soc. Rev. , 2011 , 40 , 1950 .
4.
Monfared H.H.
,
Aghapoor V.
,
Ghorbanloo M.
, and
Mayer P.
, Appl. Catal. A: Gen. , 2010 , 372 , 209 .
5.
Bahador K.
,
Morteza M.
,
Majid M.
, and
Mahnaz F.
, J. Chem. Res. , 2007 , 5 , 275 .
6.
Rydberg P.
,
Ryde U.
, and
Olsen L.
, J. Chem. Theory. Comput. , 2008 , 1369 .
7.
Karimipour G.R.
,
Shadegan H.A.
, and
Roxana A.
, J. Chem. Res. , 2007 , 252 .
8.
Xu K.W.
,
Ma J. Y.
,
Jiang Q.
,
Hu H.Y.
, and
Guo C.C.
, J. Mol. Catal. A: Chem. , 2006 , 243 , 194 .
9.
Lyons J.E.
,
Ellis P.E.
, and H.K.M. Jr., J. Catal. , 1995 , 155 , 59 .
10.
Silva G.F.
,
Silva D.C.
,
Guimaraes A.S.
,
Nascimento E.D.
,
Reboucas J.S.
,
Araujo M.P.D.
,
Carvalho M.E.M.D.D.
, and
Idemori Y.M.
, J. Mol. Catal. A: Chem. , 2007 , 266 , 274 .
11.
Karimipour G.R.
,
Morteza M.
, and
Bahador K.
, J. Chem. Res. , 2006 , 605 .
12.
Bochot C.
,
Bartoli J.F.
,
Frapart Y.
,
Dansette P.M.
,
Mansuy D.
, and
Battioni P.
, J. Mol. Catal. A: Chem. , 2007 , 263 , 200 .
13.
Molinari A.
,
Amadelli R.
,
Antolini L.
,
Maldotti A.
,
Battioni P.
, and
Mansuy D.
, J. Mol. Catal. A: Chem. , 2000 , 158 , 521 .
14.
Guo C.C.
,
Chu M.F.
,
Liu Q.
,
Liu Y.
,
Guo D.C.
, and
Liu X.Q.
, Appl. Catal. A: Gen. , 2003 , 246 , 303 .
15.
Yao Q.Z.
, Protection and new reactions in pteridine chemistry , Papierflieger-Verlag Press : Clausthal-Zellerfeld, Germany , 1997 , pp. 17 –19 .
16.
Huang G.
,
Guo C.C.
, and
Tang S.S.
, J. Mol. Catal. A: Chem. , 2007 , 261 , 125 .
17.
Lodnicka T.M.
, Metalloporphyrins in catalytic oxidations , ed.
Sheldon R.A.
, Marcel Dekker , New York , 1994 , pp. 251 .
18.
Tang H.
,
Shen C. Y.
,
Lin M.
, and
Sen A.
, Inorg. Chim. Acta , 2000 , 300 , 1109 .
19.
Haber J.
,
Matachowski L.
,
Pamin K.
, and
Poltowicz J.
, J. Mol. Catal. A: Chem. , 2003 , 198 , 215 .
20.
Nascimento E.
,
Silva G.F.
,
Caetano F.A.
,
Fernandes M.A.M.
,
Silva D.C.
,
Carvalho M.E.M.D.
,
Pernaut J.M.
,
Rebouças J.S.
, and
Idemori Y.M.
, J. Inorg. Biochem. , 2005 , 99 , 1193 .
21.
Fang Z.L.
, and
Breslow R.
, Bioorg. Med. Chem. Lett. , 2005 , 15 , 5463 .
22.
McDonald A.R.
,
Bukowski M.R.
,
Farquhar E.R.
,
Jackson T.A.
,
Koehntop K.D.
,
Seo M.S.
,
Hont R.F.D.
,
Stubna A.
,
Halfen J.A.
,
Münck E.
,
Nam W.
, and L.Q. Jr., J Am Chem. Soc. , 2010 , 132 , 17118 .
23.
Shul'pin G.B.
, J. Mol. Catal. A: Chem. , 2002 , 189 , 39 .
24.
Liu J.G.
,
Ohta T.
,
Yamaguchi S.
,
Ogura T.
,
Sakamoto S.
,
Maeda Y.
, and
Naruta Y.
, Angew. Chem. , 2009 , 121 , 942 .
25.
Sun C.G.
,
Hu B.C.
,
Zhou W.Y.
,
Xu S.C.
, and
Liu Z.L.
, Ultrason. Sonochem. , 2011 , 18 , 501 .