A one-pot two-step synthesis of tertiary alcohols combining the biocatalytic laccase/TEMPO oxidation system with organolithium reagents in aerobic aqueous media at room temperature

The one-pot/two-step combination of enzymes and polar organometallic chemistry in aqueous media is for the first time presented as a proof-of-concept study. The unprecedented combination of the catalytic oxidation of secondary alcohols by the system laccase/TEMPO with the ultrafast addition (3 s rea...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2021-12, Vol.57 (99), p.13534-13537
Main Authors: Ramos-Martín, Marina, Lecuna, Ramón, Cicco, Luciana, Vitale, Paola, Capriati, Vito, Ríos-Lombardía, Nicolás, González-Sabín, Javier, Presa Soto, Alejandro, García-Álvarez, Joaquín
Format: Article
Language:English
Subjects:
Alcohol
Alcohols
Aqueous solutions
Catalytic oxidation
Ketones
Laccase
Organometallic compounds
Oxidation
Reaction time
Reagents
Room temperature
Substrates
Synthesis
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Summary:The one-pot/two-step combination of enzymes and polar organometallic chemistry in aqueous media is for the first time presented as a proof-of-concept study. The unprecedented combination of the catalytic oxidation of secondary alcohols by the system laccase/TEMPO with the ultrafast addition (3 s reaction time) of polar organometallic reagents (RLi/RMgX) to the in situ formed ketones, run under air at room temperature, allows the straightforward and chemoselective synthesis of tertiary alcohols with broad substrate scope and excellent conversions (up to 96%). A hybrid one-pot tandem protocol combining s -block reagents with enzymes (laccase from Trametes versicolor ), in aqueous media, at room temperature and under air, is disclosed.
ISSN:1359-7345
1364-548X
DOI:10.1039/d1cc06460f