Light-promoted photocatalyst-free and redox-neutral hydrosulfonylation of unactivated alkenes using sulfinic acid

Abstract

A hydrosulfonylation reaction of unactivated alkenes with sulfinic acids was realized under light irradiation. The reaction features photocatalyst- and additive-free conditions. A diverse set of unactivated alkenes can be transformed...

EDA Complex-Promoted Cascade Cyclization of Alkynes Enabling the Rapid Assembly of 3-Sulfonylindoles and Vinyl Sulfone Oxindoles

“…Combining the results from mechanistic studies and previously reported − investigations together, we propose the following mechanism (Figure ). Initially, sodium 4-methylphenylsulfinate 2a combines with 4-methyl- N -(2-(phenylethynyl)­phenyl)­benzenesulfonamide 1a to form an EDA complex I in the presence of K 2 CO 3 . , Upon light irradiation, the generated EDA complex I undergoes a SET from the donor to the acceptor, , forming an oxygen-centered radical II-1 resonating with sulfonyl radical II-2 and an N -sulfonamide radical anion III .…”

“…The recent advent of sustainable strategies based on electron donor–acceptor (EDA) complex photoactivation enables the utilization of arylsulfinate anions as convenient sulfonyl radical precursors for the synthesis of sulfone-containing compounds by direct radical–radical coupling reactions and radical involved cascade reactions. , Driven by this burgeoning EDA chemistry, Wang and Miao developed new EDA complexes using arylsulfinate anions as electron donors and isocyanides as acceptors, providing a pathway for synthesizing C6-polyfunctionalized phenanthridines . Quite recently, Shen achieved a radical cascade cyclization with alkenes, initiated by intermolecular charge transfer between arylsulfinate anions and 2-alkynylthioanisoles via the formation of an EDA complex .…”