EDA mediated S–N bond coupling of nitroarenes and sodium sulfinate salts

Abstract

Despite their long-known photochemical properties and their industrial value, the use of nitroarenes as a productive photochemical handle in organic synthesis has remained relatively unexplored. More specifically, the photochemical formation of nitrogen-sulfur bonds from nitroarenes remains to be demonstrated. Herein, we report the design and application of a sulfinate–nitroarene electron donor–acceptor (EDA) complex and its subsequent use in the first light mediated catalyst-free synthesis of N-hydroxy-sulfonamides. The presence of the EDA was assessed spectroscopically and studied via DFT and TD-DFT calculations. A total of 32 examples including both electron withdrawing and electron donating groups were synthesized under our oxygen- and water-tolerant conditions.