Alkane Solvent-Derived Acylation Reaction Driven by Electric Fields

Electric field acceleration of alkyl hydroperoxide activationtoacylate amines in the scanning tunneling microscope-based break-junction is reported. Alkyl hydroperoxidemixtures, generated from hydrocarbon autoxidation in air, were foundto be competent reagents for the functionalization of gold surfaces.Intermolecular coupling on the surface in the presence of amines wasobserved, yielding normal alkylamides. This novel mode of alkyl hydroperoxideactivation to generate acylium equivalents was found to be responsiveto the magnitude of the bias in the break junction, indicating anelectric field influence on this novel reactivity.

Automated summary

The electric field acceleration of alkyl hydroperoxide activation to acylate amines in the scanning tunneling microscope-based break-junction is reported. It was found that alkyl hydroperoxide mixtures, generated from hydrocarbon autoxidation in air, are competent reagents for the functionalization of gold surfaces. Intermolecular coupling on the surface in the presence of amines was observed, yielding normal alkylamides. This novel mode of alkyl hydroperoxide activation is found to be responsive to the magnitude of the bias in the break junction, indicating an electric field influence on this novel reactivity.