Phototriggered Self-Catalyzed Three-Component Minisci Reaction: A Route to β-C(sp³) Heteroarylated Alcohols/Ethers

Abstract

Herein, a visible-light-triggered photocatalyst-free radical cascade Minisci reaction of heteroarenes, alkenes, and water/alcohols to obtain diverse β-C(sp3) heteroarylated alcohols/ethers has been developed. Achieved under mild and simple conditions, this protocol is scalable and features broad substrate scope and functional group tolerance. Mechanistic studies demonstrate that the heteroarene can be served as a photocatalyst to engage single-electron transfer with persulfate.

Metal- and photosensitizer-free cross-dehydrogenative coupling through photoinduced energy transfer

“…This observation rules out the possibility of heterocyclic compounds undergoing activation of oxidants via a single-electron transfer mechanism. 25…”

Photoinduced regioselective difluorination of secondary inert C(sp3)–H bonds in sulfonamides via 1,5-hydrogen-atom transfer

“…51–61 Recently, we reported a novel approach for the inert C(sp 3 )–H bond functionalization of free alcohols by employing this strategy with various heteroarenes as coupling partners. 62 Inspired by this work and our previous relevant research studies, 63–67 we hypothesized that using a 1,5-HAT strategy might enable two consecutive fluorinations at the same position of a substrate (Fig. 1C).…”

Electron‐Transfer Protocol for the Hydroxyalkenylation of Alkenes Using 1,2‐Bis(phenylsulfonyl)ethylene

“…Our research group has recently reported on the C(sp 3 )−H alkenylation of alkanes using 1,2‐bis(phenylsulfonyl)ethylene ( 2 ) [9] as an efficient radical trapping agent [10] . Encouraged by the fact that 2 exhibits excellent tolerance when exposed to the persulfate anion, which acts as a strong oxidant (+2.43 V vs. SCF), [11] we embarked on a study to develop the ET‐induced cross‐coupling of alkenes with 2 , which would lead to a regiocontrolled hydroxyalkenylation, enabling the formation of 4‐hydroxy‐1‐alkenylsulfones 3 (Scheme 1B, eq 3) [12] …”