Visible-Light-Promoted Radical Cyclization of N-Arylvinylsulfonamides: Synthesis of CF₃/CHF₂/CH₂CF₃-Containing 1,3-Dihydrobenzo[c]isothiazole 2,2-Dioxide Derivatives

Abstract

A photocatalyzed and highly efficient trifluoromethylation of N-arylvinylsulfonamides using commercially available CF₃SO₂Cl as the trifluoromethyl radical source under blue LEDs is reported. The reaction proceeds through radical cyclization under mild conditions. An investigation of the substrate scope is performed to establish a general, synthetically useful protocol for the synthesis of novel trifluoromethylated 1,3-dihydrobenzo[c]isothiazole 2,2-dioxides in moderate to high yields. This method is also successfully applied for the synthesis of difluoromethylated and trifluoroethylated 1,3-dihydrobenzo[c]isothiazole 2,2-dioxides in good to excellent yields.

Key words

N-arylvinylsulfonamides - fluoro alkyl radicals - visible light - radical cyclization - 1,3-dihydrobenzo[c]isothiazole 2,2-dioxides

Publication History

Received: 12 July 2021

Accepted after revision: 16 September 2021

Article published online:
26 October 2021

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