Ionic liquids as an alternative reaction medium for HMDST based synthesis of thioaldehydes

GRAPHICAL ABSTRACT

Abstract

Reaction of bis(trimethylsilyl)sulfide (HMDST) with aldehydes can be efficiently carried out in various ionic liquids, under CoCl₂.6H₂O or TfOTMF catalysis, leading to the formation of thioaldehydes, which are trapped as Diels-Alder cycloadducts. When 1,3-cycloheaxadiene was used, a stereoselective entry to the endo isomer was always obtained.

Keywords:

• Thioaldehydes
• ionic liquids (ILs)
• silyl sulfide
• Diels-Alder cycloadditions

Funding

Financial support from MiUR, National Project PRIN 2010–2011 “Processi ossidativi e radicalici: aspetti innovativi ed applicazioni allo sviluppo di biopolimeri melanici e antiossidanti di rilevanza biomedica e tecnologica (PROxi)” is gratefully acknowledged.