A three-component difunctionalization of N-alkenyl amides via organophotoredox radical-polar crossover

Abstract

Herein, we report a three-component organophotoredox coupling of N-alkenyl amides with α-bromocarbonyls and various nucleophiles. This transition metal-free difunctionalization protocol installs sequential C–C and C–Y (Y = S/O/N) bonds in...

Visible‐Light Promoted Radical Fluoroalkylation of O‐ and N‐Substituted Alkenes

“…In some cases, addition of triphenylphosphine (10 %) improved the yield, presumably by scavenging traces of iodine, though the way of iodine formation was not clarified. A similar reaction of N ‐vinylamides with bromodifluoroacetic ester and amide with nuclephiles such as alcohols, thiols and azide was reported [98] . In this case, cyanoarene type organic photocatalyst 4CzIPN was used.…”

“…A similar reaction of N-vinylamides with bromodifluoroacetic ester and amide with nuclephiles such as alcohols, thiols and azide was reported. [98] In this case, cyanoarene type organic photocatalyst 4CzIPN was used.…”

Transition metal-free photochemical C–F activation for the preparation of difluorinated-oxindole derivatives

“…30 The method was designed to be promoted by a hydrogen atom transfer (HAT) step via combination of diaryl ketone, thiol, and sodium formate. Continuing with our interest in the synthesis of uorinated compounds via photoredox catalysis, 19,21,22,[37][38][39] we focused on developing a metal-free preparation of diuorinated oxindole derivatives via a cascade reaction between gem-diuoromethylene radicals and N-arylmethacrylamides, exploring the photoreactive nature of thiols as photocatalysts.…”

Theoretical Underpinning of Synergetic Ir/Cu-Metallaphotoredox Catalysis in Multicomponent C–N Cross-Coupling Reactions

“…Multicomponent reactions (MCRs) provide a unique efficient tool for multiple bond formation, allowing one to access in a single reaction complex chemical compounds from simple and readily available substrates. , During the past few decades MCRs have been widely used in both academic and industrial synthetic organic chemistry. , However, this method typically requires harsh reaction conditions, heating with organometallic reagents, or high-pressure mercury lamp irradiations as an example. − To overcome these limitations, the application of recently developed photoredox-transition metal dual catalysis under mild reaction conditions has gained remarkable attention in synthetic chemistry. − …”