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Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
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Visible-Light-Promoted Synthesis of 1,3-Dicarbonyl Sulfoxonium Ylides
Radell Echemendía1, Kleber T de Oliveira2, Antonio C B Burtoloso1
1Institute of Chemistry of São Carlos, University of São Paulo, CEP, 13560-970 São Carlos, SP, Brazil.
Abstract:
A novel visible-light-promoted coupling of diazoketones with sulfoxonium ylides, employing a violet light-emitting diode, is described under both batch and continuous flow conditions. This transformation permits the direct synthesis of synthetically useful 1,3-dicarbonyl sulfoxonium ylides (33 examples, 21-85% yields), by means of an acylation from the in situ and selective generation of ketenes. The reaction performed under flow conditions proved to be very efficient, providing the 1,3-dicarbonyl sulfoxonium ylides with higher yields and shorter reaction times.
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