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. 2021 Jun 16;27(34):8704-8708.
doi: 10.1002/chem.202101056. Epub 2021 May 11.

Metal-Free Visible-Light Synthesis of Arylsulfonyl Fluorides: Scope and Mechanism

Dan Louvel  1 , Aida Chelagha  1 , Jean Rouillon  2 , Pierre-Adrien Payard  1 , Lhoussain Khrouz  2 , Cyrille Monnereau  2 , Anis Tlili  1
Affiliations

Metal-Free Visible-Light Synthesis of Arylsulfonyl Fluorides: Scope and Mechanism

Dan Louvel et al. Chemistry. .

Abstract

The first metal-free procedure for the synthesis of arylsulfonyl fluorides is reported. Under organo-photoredox conditions, aryl diazonium salts react with a readily available SO2 source (DABSO) to afford the desired product through simple nucleophilic fluorination. The reaction tolerates the presence of both electron-rich and -poor aryls and demonstrated a broad functional group tolerance. To shed the light on the reaction mechanism, several experimental techniques were combined, including fluorescence, NMR, and EPR spectroscopy as well as DFT calculations.

Keywords: arylsulfonyl fluorides; fluorine; mechanistic investigations; metal-free synthesis; organo-photoredox.

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