4.4 Article

Selective Aerobic Oxidation of Alcohols in Low Melting Mixtures and Water and Use for Telescoped One-Pot Hybrid Reactions

Journal

CHEMISTRYOPEN
Volume 11, Issue 10, Pages -

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/open.202200160

Keywords

Deep Eutectic Solvents; Water; Oxidation; Alcohols; Carbonyl compounds; Domino reactions

Funding

  1. University of Bari Aldo Moro [2017A5HXFC 002, 2020SBNHLH]
  2. Interuniversity Consortium C.I.N.M.P.I.S. [2017A5HXFC 002, 2020SBNHLH]
  3. Ministero dell'Universita e della Ricerca (MUR-PRIN) [2017A5HXFC 002, 2020SBNHLH]
  4. MCIN/AEI [PID2020-113473GB I00]
  5. Programa Severo Ochoa para la formacion en investigacion y docencia del Principado de Asturias [A-21-PF-BP20-093, PA22-PF-BP21-088]

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An efficient, selective, and sustainable catalytic method has been developed for the oxidation of activated alcohols to the corresponding carbonyl compounds. The reaction proceeds under mild conditions and yields high product yields.
An efficient, selective and sustainable protocol was developed for the CuCl2/TEMPO/TMEDA-catalyzed aerobic oxidation of activated alcohols to the corresponding carbonyl compounds using water or the environmentally friendly low melting mixture (LMM) d-fructose-urea as the reaction medium. Such oxidation reactions proceed under mild (room temperature or 40 degrees C) and aerobic conditions, with the carbonyl derivatives isolated in up to 98 % yield and within 4 h reaction time when using the above-mentioned LMM. The potential application of this methodology is demonstrated by setting up useful telescoped, one-pot two-step hybrid transformations for the direct conversion of primary alcohols either into secondary alcohols or into valuable nitroalkenes, by combining oxidation processes with nucleophilic additions promoted by highly polarized organometallic compounds (Grignard and organolithium reagents) or with nitroaldol (Henry) reactions, respectively.

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