Birch-Type Photoreduction of Arenes and Heteroarenes by Sensitized Electron Transfer

Angewandte Chemie
Anamitra Chatterjee, Burkhard König

Abstract

The direct reduction of arenes and heteroarenes by visible-light irradiation remains challenging, as the energy of a single photon is not sufficient for breaking aromatic stabilization. Shown herein is that the energy accumulation of two visible-light photons allows the dearomatization of arenes and heteroarenes. Mechanistic investigations confirm that the combination of energy-transfer and electron-transfer processes generates an arene radical anion, which is subsequently trapped by hydrogen-atom transfer and finally protonated to form the dearomatized product. The photoreduction converts planar aromatic feedstock compounds into molecular skeletons that are of use in organic synthesis.

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Citations

Jan 17, 2020·Angewandte Chemie·Felix GlaserOliver S Wenger
Jul 6, 2020·Angewandte Chemie·José A ForniAnastasios Polyzos
Jun 20, 2020·Beilstein Journal of Organic Chemistry·Stephanie G E AmosJerome Waser
Apr 3, 2020·Nature·Radek Cibulka
Oct 22, 2020·Angewandte Chemie·Yusuke MasudaMasahiro Murakami
Dec 17, 2020·Accounts of Chemical Research·Karsten Donabauer, Burkhard König
Oct 15, 2020·Angewandte Chemie·Kathiravan MurugesanBurkhard König
Aug 19, 2020·Organic Letters·Andrea SerafinoGiovanni Maestri
Mar 18, 2021·Nature Communications·Jan P MenzelChristopher Barner-Kowollik
Apr 2, 2021·ACS Central Science·Chao Zheng, Shu-Li You
Jun 3, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jun ZhouChao Chen
Jul 9, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Niklas von Wolff, Marc Robert
Jul 15, 2020·Journal of the American Chemical Society·Justin P ColeGarret M Miyake

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Methods Mentioned

BETA
NMR
phosphorescence
column chromatography

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