Solvent-free amide bond formation using a variety of methoxysilanes as coupling agent

Thomas Lainer; Frank Czerny; Michael Haas

doi:10.1039/d2ob00589a

Solvent-free amide bond formation using a variety of methoxysilanes as coupling agent

Thomas Lainer, Frank Czerny, Michael Haas^*

^*Corresponding author for this work

Institute of Inorganic Chemistry (6330)

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

Abstract

A solvent-free procedure for the formation of amides without exclusion of air and moisture is described. Using tetramethoxysilane 1, hexamethoxydisilane 2 and dodecamethoxy-neopentasilane 3 as coupling agent carboxylic acids and amines are reacted to form amides in good to excellent yields. The formation of these amides was confirmed by NMR spectroscopy and mass spectrometry. Remarkably, neopentasilane 3 exceeds the performance of the currently used monosilanes as coupling agent in terms of group tolerance and yield.

Original language	English
Pages (from-to)	3717-3720
Journal	Organic and Biomolecular Chemistry
Volume	20
Issue number	18
DOIs	https://doi.org/10.1039/d2ob00589a
Publication status	Published - 2022

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1039/d2ob00589aLicence: CC BY 4.0

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title = "Solvent-free amide bond formation using a variety of methoxysilanes as coupling agent",

abstract = "A solvent-free procedure for the formation of amides without exclusion of air and moisture is described. Using tetramethoxysilane 1, hexamethoxydisilane 2 and dodecamethoxy-neopentasilane 3 as coupling agent carboxylic acids and amines are reacted to form amides in good to excellent yields. The formation of these amides was confirmed by NMR spectroscopy and mass spectrometry. Remarkably, neopentasilane 3 exceeds the performance of the currently used monosilanes as coupling agent in terms of group tolerance and yield.",

author = "Thomas Lainer and Frank Czerny and Michael Haas",

note = "Publisher Copyright: {\textcopyright} 2022 The Royal Society of Chemistry",

year = "2022",

doi = "10.1039/d2ob00589a",

language = "English",

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AU - Czerny, Frank

AU - Haas, Michael

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N2 - A solvent-free procedure for the formation of amides without exclusion of air and moisture is described. Using tetramethoxysilane 1, hexamethoxydisilane 2 and dodecamethoxy-neopentasilane 3 as coupling agent carboxylic acids and amines are reacted to form amides in good to excellent yields. The formation of these amides was confirmed by NMR spectroscopy and mass spectrometry. Remarkably, neopentasilane 3 exceeds the performance of the currently used monosilanes as coupling agent in terms of group tolerance and yield.

AB - A solvent-free procedure for the formation of amides without exclusion of air and moisture is described. Using tetramethoxysilane 1, hexamethoxydisilane 2 and dodecamethoxy-neopentasilane 3 as coupling agent carboxylic acids and amines are reacted to form amides in good to excellent yields. The formation of these amides was confirmed by NMR spectroscopy and mass spectrometry. Remarkably, neopentasilane 3 exceeds the performance of the currently used monosilanes as coupling agent in terms of group tolerance and yield.

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ER -

Solvent-free amide bond formation using a variety of methoxysilanes as coupling agent

Abstract

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