An electron donor−acceptor (EDA) complex photoactivation strategy for radical fluorosulfonylation is disclosed for the first time. Simply upon blue light irradiation, the FSO 2 radical can be generated efficiently under catalyst-free, base-free, and additive-free conditions, which enables facile access to 6-keto alkenylsulfonyl fluorides from readily available propargyl alcohols and FSO 2 Cl. The 6-keto alkenylsulfonyl fluoride motif has been showcased as a versatile SuFEx hub with diverse follow-up derivatizations.
Sulfonyl fluorides have found diverse applications in multiple disciplines due to their reactivity and stability. Thus, exploiting the new reactivity of sulfonyl fluorides is of high importance to Sulfur (VI) Fluoride Exchange (SuFEx) chemistry. Reported herein is a three-component reaction of β-keto sulfonyl fluorides, arynes and DMF for the streamline synthesis of sulfocoumarins.The reaction proceeds by trapping of the in situ generated oquinone methides with β-keto sulfonyl fluorides, followed by selective cyclization with sulfonyl fluorides. This strategy provides a new avenue to access diverse sulfocoumarins with under mild conditions.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.