GREENER OXIDATION OF PRIMARY, SECONDARY ALCOHOLS AND DIOLS UNSING Fe(III) COMPLEX

Afnan Al-Hunaiti Teemu Niemi Timo Repo Markku leskelä
Department of Chemsitry, University of Helsinki, Helsinki

Selective oxidation of alcohols to the corresponding carbonyl compounds is a fundamental transformation in organic synthesis.1In particular, selective oxidation of alcohols to the carbonyl compounds such as primary alcohols to aldehydes or acids, or oxidation of secondary alcohols to ketones is attractive because the target molecules can be obtained directly in one-pot sequences. Many catalytic methods have been developed for oxidation of aliphatic alcohols. despite of these improvements in the catalyst development, addressing these challenges will require more efficient, cheaper, chemoselective, and greener catalyst; the low cost and non-toxicity of iron render it a particularly attractive metal in this regard.

herein a new in-situ generated iron(III) catalyst that efficiently and selectively oxidizes primary and secondary aliphatic alcohols into their corresponding carbonyl compounds acids and ketones; Even a wide range of diols are converted to the corresponding acids and ketones.

Scheme 1.Thymine acetate iron complex catalyzed oxidation of alcohols to acids and ketones.

References

1. Tojo G., and Fernandez, M.,Oxidation of primary alcohols to carboxylic acids, Springer, Berlin, 2006; Tojo, G. and Fernandez, M.Oxidation of Alcohols to Aldehydes and Ketones, Springer, Berlin, 2006; Backwall, J. E.Modern Oxidation Method,wiley-VCH, New York, 2004; M. Hudlicky,Oxidation in Organic Chemistry,Am. Chem. Soc,Washington, DC, 1990;. Sheldon R. AIn dioxygen activation and Homogeneous Catalytic Oxidation(Ed.: L. L. Simandi), Elsevier, Amestrdam, 1991, P573.

2- Al-Hunaiti A.,Niemi T., Siboueh A., Pehko P., Leskela M., Repo T. J. Chem. Comm. 2010, 46, 9250-9252.









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