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

Org Lett. 2022 Sep 9;24(35):6386-6390. doi: 10.1021/acs.orglett.2c02346. Epub 2022 Aug 26.

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.