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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.

SUBMITTER: Lasso JD

PROVIDER: S-EPMC9847664 | biostudies-literature | 2023 Jan

REPOSITORIES: biostudies-literature

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

Lasso Juan D JD Castillo-Pazos Durbis J DJ Sim Malcolm M Barroso-Flores Joaquín J Li Chao-Jun CJ

Chemical science 20221215 3

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 < ...[more]

PMID: 36741536

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