Photocatalytic Dehydrogenative Lactonization of 2-Arylbenzoic Acids

Organic Letters
Nieves P RamirezJose C Gonzalez-Gomez

Abstract

A metal-free dehydrogenative lactonization of 2-arylbenzoic acids at room temperature was developed. This work illustrates the first application of visible-light photoredox catalysis in the preparation of benzo-3,4-coumarins, an important structural motif in bioactive molecules. The combination of photocatalyst [Acr(+)-Mes] with (NH4)2S2O8 as a terminal oxidant provides an economical and environmentally benign entry to different substituted benzocoumarins. Preliminary mechanistic studies suggest that this reaction most likely occurs through a homolytic aromatic substitution pathway.

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Citations

Dec 31, 2015·Journal of the American Chemical Society·Jan B Metternich, Ryan Gilmour
Apr 9, 2016·Organic & Biomolecular Chemistry·Michael Gurry, Fawaz Aldabbagh
Jun 11, 2016·Chemical Reviews·Nathan A Romero, David A Nicewicz
Dec 10, 2016·Journal of the American Chemical Society·Satobhisha MukherjeeFrank Glorius
Mar 8, 2018·Chemistry : a European Journal·Xiang-Zhang TaoHua-Jian Xu
Nov 8, 2016·Chemical Society Reviews·Nathaniel CorriganCyrille Boyer
Nov 10, 2017·Organic & Biomolecular Chemistry·Jose C Gonzalez-GomezPedro Bonete
Jan 5, 2016·Chemical Communications : Chem Comm·Jin-Tao Yu, Changduo Pan
Jun 9, 2018·Chemistry : a European Journal·Andrea GiniOlga García Mancheño
Jan 16, 2020·Organic & Biomolecular Chemistry·Ketan WadekarVeera Reddy Yatham

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