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Mechanochemical Assembly of a Nitrile‐Based Directing Group in Arylacetic Acids Using the Passerini 3‐CR: Exploration of the Pd(II)‐Catalyzed meta‐C(sp2)−H Bond Olefination Process

The multicomponent assembly of a nitrile‐based directing group in a set of arylacetic acids under solvent‐free mechanochemical conditions using the Passerini 3‐CR and the subsequent Pd(II)‐mediated meta‐C(sp2)−H bond olefination process has been achieved. The protocol demonstrated that removing the...

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Bibliographic Details
Published in:European journal of organic chemistry 2024-05, Vol.27 (17), p.n/a
Main Authors: García‐Uribe, Juvenal, Martínez‐Flores, Sebastián, Martínez‐Barrita, Valeri, Polindara‐García, Luis A.
Format: Article
Language:English
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Summary:The multicomponent assembly of a nitrile‐based directing group in a set of arylacetic acids under solvent‐free mechanochemical conditions using the Passerini 3‐CR and the subsequent Pd(II)‐mediated meta‐C(sp2)−H bond olefination process has been achieved. The protocol demonstrated that removing the DG under mild conditions from the activated Passerini adducts affords a novel N‐(tert‐butyl)‐2‐(2‐cyanophenyl)‐2‐hydroxyacetamide, which can be re‐utilized in the future as DG in other distal activation processes. A practical solvent‐free mechanochemical protocol for installing a nitrile‐based directing group in arylacetic acids through the Passerini 3‐CR and the subsequent Pd(II)‐mediated meta‐C(sp2)−H olefination process has been developed.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202301320