One-pot conversion of primary alcohols to α-oxygenated alkanals with TEMPO in combination with molecular oxygen and ruthenium complex

Reaction of primary alcohols with an oxidizing system composed of 4-BzO'TEMPO (2 equiv.), RuCl 2(PPh 3) 3 as a catalyst, and molecular oxygen leads to concomitant oxidation and substitution, giving the corresponding α-oxygenated alkanals. Similar reaction of secondary alcohols terminates at the...

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Bibliographic Details
Published in:Tetrahedron letters 1995-05, Vol.36 (18), p.3223-3226
Main Authors: Inokuchi, Tsutomu, Nakagawa, Keiichi, Torii, Sigeru
Format: Article
Language:English
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Summary:Reaction of primary alcohols with an oxidizing system composed of 4-BzO'TEMPO (2 equiv.), RuCl 2(PPh 3) 3 as a catalyst, and molecular oxygen leads to concomitant oxidation and substitution, giving the corresponding α-oxygenated alkanals. Similar reaction of secondary alcohols terminates at the stage of oxidation of hydroxyl group, forming the ketones, selectively. Primary alcohols is oxidized to the α-oxygenated alkanals in a molecular oxygen, 4-BzOTEMPO, and RuCl 2(PPh 3) 3 (catalytic) system.
ISSN:0040-4039
1873-3581
DOI:10.1016/0040-4039(95)00519-I