Photo-on-Demand Synthesis of Vilsmeier Reagents with Chloroform and Their Applications to One-Pot Organic Syntheses.

摘要: The Vilsmeier reagent (VR), first reported a century ago, is versatile in variety of organic reactions. It used extensively formylation However, the synthesis VR generally requires highly toxic and corrosive reagents such as POCl3, SOCl2, or COCl2. In this study, we found that readily obtained from CHCl3 solution containing N,N-dimethylformamide N,N-dimethylacetamide upon photo-irradiation under O2 bubbling. corresponding were high yields with generation gaseous HCl CO2 byproducts to allow their isolations crystalline solid products amenable analysis by X-ray crystallography. With advantage using CHCl3, which bifunctionally serves reactant solvent, photo-on-demand available for one-pot syntheses aldehydes, acid chlorides, formates, ketones, esters, amides.