Chemoselective aerobic oxidation of 4-allylanisol by Fe(III) porphyrins in an aqueous system

Vakuliuk, O.; Mutti, F.G.; Lara, M.; Gryko, D.T.; Kroutil, W.;

Tetrahedron Lett., 2011, 52, 3555 – 3557. DOI: 10.1016/j.tetlet.2011.03.050

2011_tetrahedron

The allyl moiety of 4-allyl-anisol was oxidized in the presence of a Fe(III) porphyrin derivative to the corresponding α,β-unsaturated aldehyde in an initial oxidation step with perfect chemoselectivity. Molecular oxygen was employed as the sole environmental innocuous oxidant. The reaction was performed in an aqueous buffer/CH2Cl2 mixture using the detergent Tween 80 to homogenize the system.

 
 
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