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Electrostatically tuned phenols: a scalable organocatalyst for transfer hydrogenation and tandem reductive alkylation of <i>N</i>-heteroarenes

Brijesh Patel, Shilpa Dabas, Parth Patel, Saravanan Subramanian

2022Chemical Science21 citationsDOIOpen Access PDF

Abstract

-arenes using the Hantzsch ester as a hydride source. The biomimetic catalyst (1-5 mol%) displays potential catalytic activity to prepare diverse tetrahydroquinoline derivatives with good to excellent conversion under ambient reaction conditions. Kinetic studies reveal that the ETP is 130-fold faster than the uncharged counterpart, towards completion of the reaction. Control experiments and NMR spectroscopic investigations elucidate the role of the charged environment in the catalytic transformation.

Topics & Concepts

CatalysisChemistryCombinatorial chemistryTandemSubstrate (aquarium)AlkylationHydrideTransfer hydrogenationPhenolsCovalent bondOrganic chemistryMaterials scienceComposite materialHydrogenRutheniumOceanographyGeologyAsymmetric Hydrogenation and CatalysisChemical Synthesis and AnalysisAsymmetric Synthesis and Catalysis
Electrostatically tuned phenols: a scalable organocatalyst for transfer hydrogenation and tandem reductive alkylation of <i>N</i>-heteroarenes | Litcius