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Visible-Light-Promoted Synthesis of 1,3-Dicarbonyl Sulfoxonium Ylides.

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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… Click to show full 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.

Keywords: sulfoxonium; light promoted; synthesis; dicarbonyl sulfoxonium; visible light; sulfoxonium ylides

Journal Title: Organic letters
Year Published: 2022

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