Hydration of nitriles using a metal-ligand cooperative ruthenium pincer catalyst

Nitrile hydration provides access to amides that are important structural elements in organic chemistry. Here we report catalytic nitrile hydration using ruthenium catalysts based on a pincer scaffold with a dearomatized pyridine backbone. These complexes catalyze the nucleophilic addition of H 2 O...

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Bibliographic Details
Published in:Chemical science (Cambridge) Vol. 1; no. 45; pp. 1647 - 1652
Main Authors: Guo, Beibei, de Vries, Johannes G, Otten, Edwin
Format: Journal Article
Language:English
Published: England Royal Society of Chemistry 07.12.2019
Subjects:
Additives
Aliphatic compounds
Amides
Catalysts
Chemistry
Hydration
Ligands
Nitriles
Organic chemistry
Room temperature
Ruthenium
Structural members
ISSN:2041-6520, 2041-6539
Online Access:Get full text
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Summary:Nitrile hydration provides access to amides that are important structural elements in organic chemistry. Here we report catalytic nitrile hydration using ruthenium catalysts based on a pincer scaffold with a dearomatized pyridine backbone. These complexes catalyze the nucleophilic addition of H 2 O to a wide variety of aliphatic and (hetero)aromatic nitriles in t BuOH as solvent. Reactions occur under mild conditions (room temperature) in the absence of additives. A mechanism for nitrile hydration is proposed that is initiated by metal-ligand cooperative binding of the nitrile. The hydration of a broad range of aliphatic and (hetero)aromatic nitriles is reported via catalysis by metal-ligand cooperative Ru pincer complexes under very mild conditions.
Bibliography:10.1039/c9sc04624k
Electronic supplementary information (ESI) available. See DOI
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ISSN:2041-6520
2041-6539
DOI:10.1039/c9sc04624k