Organophotoredox‐Catalyzed Decarboxylative N‐Alkylation of Sulfonamides

Abstract

This publication is part of a joint Special Collection with EurJIC on "Main Group Catalysis". Please check the ChemCatChem homepage for more articles in the collection.

Organophotoredox-catalyzed semipinacol rearrangement via radical-polar crossover

“…Our group has made ongoing contributions to the development of organophotoredox catalysis enabling redox neutral RPC processes 22 – 25 . A phenothiazine photoredox catalyst allows the generation of an alkyl radical by single electron reduction of aliphatic carboxylic acid-derived N -acyloxyphthalimides under visible light irradiation.…”

“…Based on our previous reports 22 – 25 on the phenothiazine-based organophotoredox catalysis, plausible pathways are outlined in Fig. 4 .…”

Extended phenothiazines: synthesis, photophysical and redox properties, and efficient photocatalytic oxidative coupling of amines

“…[9][10][11][12][13][14][15] Moreover, phenothiazine derivatives have also been proven to be effective photoredox catalysts for various synthetic transformations ranging from metal-free atom transfer radical polymerization (ATRP) for controlled polymer synthesis [16][17][18][19][20][21][22][23] to small molecule transformations such as radical dehalogenations, 24 nucleophilic alkoxylations of alkyl olens, 25 photoredox catalyzed C-N and C-H/C-H cross-couplings, 26,27 and so on. 28,29 Despite these diverse electronic and optical properties and wide applications, the development of phenothiazine-based materials is limited primarily to the chemical modication of the phenothiazine core at N, S sides and 3, 7 positions (Fig. 1).…”

A Triple Photoredox/Cobalt/Brønsted Acid Catalysis Enabling Markovnikov Hydroalkoxylation of Unactivated Alkenes

“…We established our working hypothesis of a triple photoredox/cobalt/Brønsted acid catalysis for Markovnikov hydroalkoxylation of alkenes (Scheme C). , Under visible light irradiation, photoredox catalyst A becomes the excited state B bearing high reducing ability, which undergoes a single electron transfer to Co­(II) ( C ) to form a radical ion pair ( D ). Next, a weak Brønsted acid decomposes D into Co­(III) hydride ( E ) and a radical cation of photoredox catalyst F .…”