4.7 Article

Lanthanide-oxo clusters for efficient catalytic reduction of carboxamides

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SCIENCE CHINA-CHEMISTRY
卷 66, 期 2, 页码 443-448

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SCIENCE PRESS
DOI: 10.1007/s11426-022-1493-y

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lanthanide clusters; amide reduction; metal-hydride; BH3; catalytic mechanism

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In this study, polynuclear lanthanide-oxo clusters Ln(16) (Ln = Eu and Gd) were used as efficient catalysts for the reduction of primary and secondary carboxamides to amines, with yields ranging from 71% to 98% and a broad substrate scope. The methodology was further applied to the gram-scale synthesis of phenethylamine drug with a yield of 93%. Through the isolation and characterization of catalytic intermediates, a catalytic mechanism involving multipath reaction was proposed. This work provides efficient lanthanide cluster catalysts for the reduction of carboxamides to amines.
The reduction of carboxamides into high value-added amines is a very interesting but great challenging topic. Herein we demonstrate that polynuclear lanthanide-oxo clusters Ln(16) (Ln = Eu and Gd) can be used as efficient catalyst to reduce primary and secondary carboxamides to amines with excellent yield of 71%-98% and broad substrates scope. The methodology can extend to the gram-scale synthesis of phenethylamine drug with 93% yield. Based on the isolation and characterization of catalytic intermediates, a catalytic mechanism involving multipath reaction is proposed. This work provides efficient lanthanide cluster catalysts for the reduction of carboxamides to amines.

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