Silver-catalyzed monofluoromethylation of alkynoates with sodium monofluoroalkanesulfinate (CH₂FSO₂Na) to access 3-monofluoromethylated coumarins

Abstract

A silver-catalyzed cascade radical monofluoromethylation/5-exo cyclization/ester migration of alkynoates with sodium monofluoromethanesulfinate (CH₂FSO₂Na) to give a variety of 3-monofluoromethylated coumarins was investigated. The reaction was effectively promoted by silver catalyst and K₂S₂O₈. Moreover, this method exhibits simplified operation, mild reaction conditions and excellent functional group compatibility.

GRAPHICAL ABSTRACT

Keywords:

• Alkynoate
• cascade reaction
• coumarins
• monofluoromethylation
• silver-catalyzed

Additional information

Funding

The Intercollegiate Key Scientific Research Projects of Henan Province [17B150006], the Science and Technology Research Project of Henan Province [172102310332], the aid Project for the Leading Young Teachers in Henan Provincial Institutions of Higher Education of China [2016GGJS-118] are warmly acknowledged for funding this work.