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Synthesis of 3-SCF2H-/3-SCF3-chromones via Interrupted Pummerer Reaction/Intramolecular Cyclization Mediated by Difluoromethyl or Trifluoromethyl Sulfoxide and Tf2O.

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The reaction of alkynyl aryl ketones bearing an o-methoxy group with difluoromethyl sulfoxide in the presence of Tf2O was found to conveniently afford the corresponding 3-SCF2H-substituted chromones. The combining use… Click to show full abstract

The reaction of alkynyl aryl ketones bearing an o-methoxy group with difluoromethyl sulfoxide in the presence of Tf2O was found to conveniently afford the corresponding 3-SCF2H-substituted chromones. The combining use of difluoromethyl sulfoxide/Tf2O could represent the first reagents system that can introduce the biologically important SCF2H moiety under base-free conditions via an interrupted Pummerer reaction. The same protocol could also be applied to the synthesis of 3-SCF3-substituted chromones by replacing difluoromethyl sulfoxide with trifluoromethyl sulfoxide and CH3CN with toluene.

Keywords: reaction; sulfoxide tf2o; via interrupted; sulfoxide; interrupted pummerer

Journal Title: Organic letters
Year Published: 2022

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