Synthesis and characterization of rare-earth metallate amido complexes bearing the 2-amidate-functionalized indolyl ligand and their application in the hydroboration of esters with pinacolborane

In this work, the molecular aluminium dihydride complex bearing an N, N’‐chelated conjugated bis‐guanidinate (CBG) ligand is used as a catalyst for reducing a wide range of aryl and alkyl esters with good tolerance of alkene (C=C), alkyne (C≡C), halides (Cl, Br, I and F), nitrile (C≡N), and nitro (NO2) functionalities. Further, we investigated the catalytic application of aluminium dihydride in the C−O bond cleavage of alkyl and aryl epoxides into corresponding branched Markovnikov ring‐opening products. In addition, the chemoselective intermolecular reduction of esters over other reducible functional groups, such as amides and alkenes, has been established. Intermediates are isolated and characterized by NMR and HRMS studies, which confirm the probable catalytic cycles for the hydroboration of esters and epoxides.

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Aluminium‐Catalyzed Selective Hydroboration of Esters and Epoxides to Alcohols: C−O Bond Activation

Sarkar

Sahoo

Nembenna

2022

Chemistry A European J

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Unusual selective reactivity of the rare-earth metal complexes bearing a ligand with multiple functionalities

Hong

Rajeshkumar²,

Zhu³

et al. 2022

Sci. China Chem.

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Zinc Catalyzed Hydroboration of Esters and Nitriles with Pinacolborane

Kumar,

et al. 2023

J. Org. Chem.

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Synthesis and characterization of rare-earth metallate amido complexes bearing the 2-amidate-functionalized indolyl ligand and their application in the hydroboration of esters with pinacolborane

Abstract: The reactions of 2-amidate-functionalized indolyl proligand 2-(2,6-iPr2C6H3NHC=O)C8H5NH (H2L) with [(Me3Si)2N]3RE(μ-Cl)Li(THF)3 were studied leading to the synthesis and characterization of a series of novel discrete trinuclear rare-earth metal metallate amido complexes...

Cited by 6 publications

References 92 publications

Aluminium‐Catalyzed Selective Hydroboration of Esters and Epoxides to Alcohols: C−O Bond Activation

Aluminium‐Catalyzed Selective Hydroboration of Esters and Epoxides to Alcohols: C−O Bond Activation

Unusual selective reactivity of the rare-earth metal complexes bearing a ligand with multiple functionalities

Zinc Catalyzed Hydroboration of Esters and Nitriles with Pinacolborane

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