Direct oxygenation of nonactivated aliphatic C(sp)-H groups with peroxycarboxylic acids in the presence of palladium tris(pyridylmethyl)amine complex (0.6 mol %) is reported, providing the corresponding hydroxylated derivatives in up to 94% yields. The oxidation of 3° C-H groups occurs stereospecifically, with the catalyst system demonstrating extremely high sensitivity to electronic effects (adamantane oxidation: 3°:2° up to >300). This suggests potential applications for the 3°-regioselective oxidative functionalization of complex molecules of natural origin.
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| http://dx.doi.org/10.1021/acs.orglett.2c04371 | DOI Listing |
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