Metal-Free Visible-Light Synthesis of Arylsulfonyl Fluorides: Scope and Mechanism
Dan Louvel1, Aida Chelagha1, Jean Rouillon2
1Institute of Chemistry and Biochemistry (ICBMS-UMR CNRS 5246), Univ Lyon, Université Lyon 1, CNRS, CPE-Lyon, INSA 43 Bd du 11 Novembre 1918, 69622, Villeurbanne, France.
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.
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