Hydroquinone/Quinone Cycle for Reductive Photocatalytic Transformations
Iida Alanko, Anna Lenarda, Xinyu Bao, Alice Genovese, Juan V. Alegre-Requena, Juho Helaja
TL;DR
Scientists developed a new photocatalytic method using hydroquinone/quinone cycles to efficiently deoxygenate N-heterocyclic compounds under visible light.
Contribution
The study introduces a novel visible-light-driven reductive photocatalytic system using hydroquinone/quinone cycles with alcohols as hydrogen sources.
Findings
Phenanthrenehydroquinones act as catalytic organic photoreductants under visible light.
The system efficiently deoxygenates N-heterocyclic N-oxides with lower reduction potentials than the catalyst.
TD-DFT calculations show H2PQs function as both photoacids and photoreductants.
Abstract
Phenanthrenehydroquinones (H2PQs), generated in situ from phenanthrenequinones under visible light using alcohols as hydrogen sources, act as catalytic organic photoreductants. They deoxygenate efficiently diverse N-heterocyclic N-oxides, including substrates having more negative reduction potentials than the H2PQ excited-state reduction potential ( EH2PQ+·/H2PQ* = −2.10 V vs SCE), suggesting hydrogen bonding assisted electron transfer. TD-DFT calculations indicate H2PQs act as both photoacids and photoreductants. This work demonstrates the harnessing of the hydroquinone/quinone cycle in visible-light-driven reductions.
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Taxonomy
TopicsRadical Photochemical Reactions · Photochromic and Fluorescence Chemistry · Catalytic C–H Functionalization Methods