Visible-Light-Induced Decarboxylation Coupling/Intramolecular Cyclization: A One-Pot Synthesis for 4-Aryl-2-quinolinone Derivatives

Abstract

A visible-light-induced decarboxylation coupling/intramolecular cyclization is reported. The one-pot synthesis system provides mild, efficient, and atom economical access to the synthesis of 4-aryl-2-quinolinone derivatives. It is notable that the necessary oxidant in the traditional decarboxylation coupling is replaced by the visible-light irradiation in this paper. In addition, the HBV inhibitor is synthesized by the one-pot synthesis system in an atom economical manner.

Visible‐Light‐Triggered, Metal‐ and Photocatalyst‐Free Acylation of N‐Heterocycles

“…Significantly stronger absorption band was detected in near UV‐light (λ>300 nm) with shoulder up to 380 nm for 1 a . This result seems coherent with the observed slow photodecarboxylation and generation of the acyl radical when reacting 1 a with TEMPO (Scheme c) . Furthermore, as 1 a absorbs weakly within 330–380 nm range, a standard acylation reaction was performed using UV−A pen as a light source (λ=315–400 nm; λ max =365 nm).…”

Visible-Light-Driven Organic Photochemical Reactions in the Absence of External Photocatalysts

“…In 2016, Ma, Yu, and co-workers reported a halogen bond (XB) enabled visible-light-irradiated isocyanide insertion. 68a The EDA complex was clearly verified by 19 F NMR titration experiments and Job's method. A visible-light-induced electron transfer enables the generation of R F radical A, providing a variety of 2-fluoroalkylated quinoxalines 241 after double radical isocyanide insertion steps (Scheme 99).…”

“…Chu and co-workers reported a decar-boxylative coupling/intramolecular cyclization cascade between tetrahydroquinolines 52 and 2-aryl-2-oxoacetic acids 53 induced by visible light (Scheme 18). 19 The one-pot procedure represents a mild and efficient way to approach various 4-arylquinolin-2-ones 54. It is noteworthy that the current protocol can be utilized for the synthesis of an HBV inhibitor.…”

Recent Advances in Photoredox Methods for Ketone Synthesis

“…Recently, 4‐aryl‐2‐quinolinone derivatives have also been synthesized via decarboxylative coupling of α − keto acids with N‐ acetyl‐1,2,3,4‐tetrahydroquinolines (Scheme ) . The reaction involves the direct formation of acyl radical from aryl glyoxylic acid under visible light irradiation evidenced by TEMPO trapping experiment.…”