Continuous Flow Oxidation of Alcohols Using TEMPO/NaOCl for the Selective and Scalable Synthesis of Aldehydes.
Parth NaikJorge García-LacunaPatrick O'NeillMarcus BaumannPublished in: Organic process research & development (2023)
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.
Keyphrases
- antiretroviral therapy
- hydrogen peroxide
- hiv infected
- human immunodeficiency virus
- hiv positive
- randomized controlled trial
- hepatitis c virus
- electron transfer
- hiv aids
- ionic liquid
- emergency department
- hiv testing
- adverse drug
- risk assessment
- human health
- climate change
- drug induced
- amino acid
- molecularly imprinted
- mass spectrometry