Photoinduced, metal- and photosensitizer-free decarboxylative C–H (amino)alkylation of heteroarenes in a sustainable solvent

Abstract

Herein, a metal- and photosensitizer-free protocol has been developed for decarboxylative C−H (amino)alkylation of heteroarenes using carboxylic acids as (amino)alkylating reagents. This reaction is performed in a sustainable solvent (dimethyl...

α-Amino Radical-Mediated Difunctionalization of Alkenes with Polyhaloalkanes and N-Heteroarenes

“…On the basis of the results presented above and previous work, − we propose a plausible reaction mechanism (Scheme ). Initially, the tert -butoxy radical is formed by the Cu­(I)-catalyzed decomposition of TBHP, which reacts with another molecule of TBHP to generate the tert -butylperoxyl radical.…”

“…Recently, our group focused on the modification of N -heteroarenes through the multicomponent reaction . In 2021, we developed a novel method for the synthesis of ( E )-quinoxalinone oximes using quinoxalinones, tert -butyl nitrite (TBN), and ketones as the starting materials through a multicomponent reaction .…”

Iron-Catalyzed Photoredox Intermolecular Dearomatization of Benzothiazoles with Alkanes

“…In recent years, photoredox-catalyzed reactions have been extensively explored in organic synthesis; − especially, visible-light-mediated dearomatization strategies have been employed as appealing alternatives for synthesis of heterocyclic frameworks. − A series of aromatic compounds, such as indole, − benzofuran, and benzothiophene, have been achieved in intermolecular or intramolecular dearomatization processes by the visible light irradiation (Scheme b). However, generally speaking, the current research mainly focuses on aromatic heterocycles containing only one heteroatom, especially indole and its derivatives; other heteroaromatic rings containing two heteroatoms are relatively less explored.…”

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

“…Using the modified Hofmann-Löffler-Freytag (HLF) reaction involving 1,5-hydrogen-atom transfer (1,5-HAT) is a potent and promising way to activate inert C(sp 3 )-H bonds, [45][46][47][48][49][50] which can functionalize remote C-H bonds in a site-selective manner. [51][52][53][54][55][56][57][58][59][60][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.…”