Novel Insights into the Combination of Metal‐ and Biocatalysis: Cascade One‐Pot Synthesis of Enantiomerically Pure Biaryl Alcohols in Deep Eutectic Solvents

One of the pioneering examples of chemoenzymatic cascades in water such as the palladium‐catalysed Suzuki‐cross coupling followed by an enzymatic reduction has been revisited by the employment of a medium containing Deep Eutectic Solvents (DESs) for the catalytic performance. Thus, the unique proper...

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Bibliographic Details
Published in:ChemCatChem 2018-10, Vol.10 (19), p.4417-4423
Main Authors: Paris, Juraj, Ríos‐Lombardía, Nicolás, Morís, Francisco, Gröger, Harald, González‐Sabín, Javier
Format: Article
Language:English
Subjects:
Alcohol
alcohol dehydrogenase
Alcohols
cascade reactions
Cascades
Catalysis
chemoenzymatic synthesis
Cross coupling
deep eutectic solvents
Palladium
Solvents
Substrates
Suzuki coupling
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Summary:One of the pioneering examples of chemoenzymatic cascades in water such as the palladium‐catalysed Suzuki‐cross coupling followed by an enzymatic reduction has been revisited by the employment of a medium containing Deep Eutectic Solvents (DESs) for the catalytic performance. Thus, the unique properties of these neoteric solvents enabled to reach high substrate concentration for the overall process. Moreover, both isolated enzymes and whole cells exhibited excellent activities which allowed to obtain a set of chiral biaryl alcohols in good yields and very high enantiomeric excess (>99 %). Pd goes biorenewable! A mixture of deep eutectic solvent (DES) and aqueous buffer proved to be an optimal medium for performing a chemoenzymatic cascade consisting of a palladium‐catalysed Suzuki cross‐coupling followed by an enzymatic reduction. Owing to the unique features of DESs, the process could be run at high concentration for both steps, enabling a variety of biarylic alcohols with very high conversion and enantiomeric excess.
ISSN:1867-3880
1867-3899
DOI:10.1002/cctc.201800768