Selective oxidation of primary alcohols mediated by nitroxyl radical in aqueous solution. Kinetics and mechanism
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Nitroxyl radical-catalyzed chemoselective alcohol oxidation for the synthesis of polyfunctional molecules
2020, Tetrahedron LettersCitation Excerpt :Although MnO2 oxidation has been widely applied in the chemoselective oxidation of benzylic and allylic alcohols in the presence of aliphatic alcohols [19], several successful applications of TEMPO-catalyzed oxidation reaction toward this chemoselective oxidation have also been reported. Essigmann and Kobertz reported the chemoselective oxidation of the primary benzylic alcohol in 14 during the synthesis of a cis-syn furan-side photoproduct formed from a psoralen derivative and thymidine (Fig. 7) [20]. The chemoselective oxidation proceeded in the presence of primary aliphatic alcohol and phenol using oxygen, TEMPO, and CuCl to afford aldehyde 15 in 70% yield.