Solvent-free amide bond formation using a variety of methoxysilanes as coupling agent
Thomas Lainer, Frank Czerny, Michael Haas
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.
Topics & Concepts
ChemistryYield (engineering)AmideSolventCoupling (piping)Mass spectrometryNuclear magnetic resonance spectroscopyPeptide bondCombinatorial chemistryOrganic chemistryPolymer chemistryChromatographyMechanical engineeringMaterials scienceMetallurgyEngineeringEnzymeChemical Synthesis and AnalysisChemical Synthesis and ReactionsSynthetic Organic Chemistry Methods