Continuous Flow Oxidation of Alcohols Using TEMPO/NaOCl for the Selective and Scalable Synthesis of Aldehydes

A simple and benign continuous flow oxidation protocol for the selective conversion of primary and secondary alcohols into their respective aldehyde and ketone products is reported. This approach makes use of catalytic amounts of TEMPO in combination with sodium bromide and sodium hypochlorite in a...

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Bibliographic Details
Published inOrganic process research & development Vol. 28; no. 5; pp. 1587 - 1596
Main Authors Naik, Parth, García-Lacuna, Jorge, O’Neill, Patrick, Baumann, Marcus
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 17.05.2024
Subjects
scale-up
continuous flow
aldehyde
TEMPO-oxidation
in-line extraction
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Summary:A simple and benign continuous flow oxidation protocol for the selective conversion of primary and secondary alcohols into their respective aldehyde and ketone products is reported. This approach makes use of catalytic amounts of TEMPO in combination with sodium bromide and sodium hypochlorite in a biphasic solvent system. A variety of substrates are tolerated including those containing heterocycles based on potentially sensitive nitrogen and sulfur moieties. The flow approach can be coupled with inline reactive extraction by formation of the carbonyl-bisulfite adduct which aids in separation of remaining substrate or other impurities. Process robustness is evaluated for the preparation of phenylpropanal at decagram scale, a trifluoromethylated oxazole building block as well as a late-stage intermediate for the anti-HIV drug maraviroc which demonstrates the potential value of this continuous oxidation method.
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ISSN:1083-6160
1520-586X
DOI:10.1021/acs.oprd.3c00237