Abstract
Four chiral manganese(III)-salen complexes (1–4) were employed as catalysts in the oxidation of hydrocarbons at room temperature using pentafluoroiodosylbenzene as terminal oxidant. The reactions were carried out in acetonitrile and dichloromethane. Norbornene has been selectively oxidized to exo-epoxynorborane in 85% yield. At room temperature, oxygenation of cyclohexane up to 14% in acetonitrile medium has also been achieved.
Similar content being viewed by others
References
Williams RJP (2008) J Inorg Biochem 102:1
Labinger JA, Bercaw JE (2002) Nature 417:507
Jia C, Kitamura T, Fujiwara Y (2001) Acc Chem Res 34:633
Sheldon RA, Kochi JK (eds) (1981) Metal-catalyzed oxidations of organic compounds. Academic, New York
Nam W (2007) Acc Chem Res 40:522
Lindoy LF (1989) The chemistry of macrocyclic ligand complexes. Cambridge University Press, Cambridge
Ortiz de Montellano PR (ed) (1976) Cytochrome P-450: structure, mechanism and biochemistry. Plenum, New York
Cozzi PG (2004) Chem Soc Rev 33:410
Che CM, Huang JS (2009) Chem Commun 3996
Dalton CT, Ryan KM, Wall VM, Bousquet C, Gilheany DG (1999) Top Catal 5:75
Katsuki T (1996) J Mol Catal A: Chem 113:87
Katsuki T (1995) Coord Chem Rev 140:189
Mansuy D (2007) C R Chimie 10:92
Srinivasan K, Michaud P, Kochi JK (1986) J Am Chem Soc 108:2309
Yoon H, Wagler TR, O’Connor KJ, Burrows CJ (1990) J Am Chem Soc 112:4568
Zhang W, Loebach JL, Wilson SR, Jacobsen EN (1990) J Am Chem Soc 112:2801
Zhang W, Jacobsen EN (1991) J Org Chem 56:2296
Jacobsen EN (1993) In: Ojima I (ed) Catalytic asymmetric synthesis. VCH, New York
Finney NS, Pospisil PJ, Chang S, Palucki M, Konsler RJ, Hansen KB, Jacobsen EN (1997) Angew Chem Int Ed Engl 36:1720
Silva AR, Freire C, de Castro B (2004) New J Chem 28:253
Rispens MT, Meetsma A, Feringa BL (1994) Recl Trav Chim Pays-Bas 113:413
Bai Y, Chiniwalla P, Elce E, Shick RA, Sperk J, Ann S, Allen B, Kohl PA (2004) J Appl Polym Sci 91:3023
Kamata K, Yonehara K, Sumida Y, Yamaguchi K, Hikichi S, Mizuno S (2003) Science 300:964
Patel SA, Sinha S, Mishra AN, Kamath BV, Ram RN (2003) J Mol Catal A: Chem 192:53
Monnier JR (2001) Appl Catal A 221:73
Raj NKK, Ramaswamy AV, Manikandan P (2005) J Mol Catal A: Chem 227:37
Leung WH, Che CM, Yeung CH, Poo CK (1993) Polyhedron 12:2331
Palucki M, Finney NS, Pospisil PJ, Güller ML, Ishida T, Jacobsen EN (1998) J Am Chem Soc 120:948
Linker T (1997) Angew Chem Int Ed Engl 36:2060
Biswas AN, Das P, Kandar SK, Agarwala A, Bandyopadhyay D, Bandyopadhyay P (2009) Catal Commun 10:708
Saji PV, Ratnasamy C, Gopinathan S US Patent 6,392,093B1
Acknowledgments
The financial support (SR/S1/IC-08/2007) from DST, Government of India, is gratefully acknowledged.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Biswas, A.N., Das, P., Kandar, S.K. et al. Chiral Mn(III) salen catalyzed oxidation of hydrocarbons. Transition Met Chem 35, 527–530 (2010). https://doi.org/10.1007/s11243-010-9359-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11243-010-9359-9