Mild amidation of aldehydes with amines mediated by lanthanide catalysts

Sung Yong Seo; Tobin J. Marks

doi:10.1021/ol702788j

Mild amidation of aldehydes with amines mediated by lanthanide catalysts

Sung Yong Seo, Tobin J. Marks

Northwestern University

Research output: Contribution to journal › Article › peer-review

174 Citations (Scopus)

Abstract

(Chemical Equation Presented) Catalytic amidation of aldehydes with amines is efficiently mediated by homoleptic lanthanide amido complexes, Ln[N(SiMe ₃)₂]₃ (Ln = La, Sm, and Y). Amidation reactivity follows the trend: La > Sm ≈ Y. These reactions proceed in high yield without added oxidants, bases, and/or heat or light, which are usually required in other catalytic amidation processes. The reaction is demonstrated with a variety of amines, with yields as high as 98% based on amine.

Original language	English
Pages (from-to)	317-319
Number of pages	3
Journal	Organic Letters
Volume	10
Issue number	2
DOIs	https://doi.org/10.1021/ol702788j
Publication status	Published - Jan 17 2008

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "(Chemical Equation Presented) Catalytic amidation of aldehydes with amines is efficiently mediated by homoleptic lanthanide amido complexes, Ln[N(SiMe 3)2]3 (Ln = La, Sm, and Y). Amidation reactivity follows the trend: La > Sm ≈ Y. These reactions proceed in high yield without added oxidants, bases, and/or heat or light, which are usually required in other catalytic amidation processes. The reaction is demonstrated with a variety of amines, with yields as high as 98% based on amine.",

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N2 - (Chemical Equation Presented) Catalytic amidation of aldehydes with amines is efficiently mediated by homoleptic lanthanide amido complexes, Ln[N(SiMe 3)2]3 (Ln = La, Sm, and Y). Amidation reactivity follows the trend: La > Sm ≈ Y. These reactions proceed in high yield without added oxidants, bases, and/or heat or light, which are usually required in other catalytic amidation processes. The reaction is demonstrated with a variety of amines, with yields as high as 98% based on amine.

AB - (Chemical Equation Presented) Catalytic amidation of aldehydes with amines is efficiently mediated by homoleptic lanthanide amido complexes, Ln[N(SiMe 3)2]3 (Ln = La, Sm, and Y). Amidation reactivity follows the trend: La > Sm ≈ Y. These reactions proceed in high yield without added oxidants, bases, and/or heat or light, which are usually required in other catalytic amidation processes. The reaction is demonstrated with a variety of amines, with yields as high as 98% based on amine.

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