Synfacts 2006(12): 1277-1277  
DOI: 10.1055/s-2006-955616
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Arylation and Oxidative Esterification of Aldehydes with Siloxanes

Contributor(s): Paul Knochel, Andrei Gavryushin
R. Lerebours, C. Wolf*
Georgetown University, Washington D.C., USA
Further Information

Publication History

Publication Date:
22 November 2006 (online)

Significance

This paper describes two novel interesting reactions of aryltrialkoxysilanes: nucleophilic 1,2-addition of the aryl moiety to aldehydes and the oxidation of aldehydes by alkoxysilanes to the corresponding esters, promoted by palladium-phosphinous acid catalytic species. Since aryltrimethoxysilanes are stable, easy-to-handle compounds, the first reaction can serve as a convenient synthetic way to diarylcarbinols. In the second process, cheap Si(OMe)4 can be used as the oxidant, which makes this method very attractive for the direct transformation of aldehydes into the corresponding methyl esters.