A trick of the Mallory reaction of 2,3-diaryl-substituted naphthoquinones: a primary photoproduct as a reductant

A trick of the Mallory reaction of 2,3-diaryl-substituted naphthoquinones: a primary photoproduct as a reductant Full article

Journal

Journal of Photochemistry and Photobiology A: Chemistry
ISSN: 1010-6030 , E-ISSN: 1873-2666

Output data

Year: 2026, Volume: 477, Article number : 117113, Pages count : 5 DOI: 10.1016/j.jphotochem.2026.117113

Tags

Naphthoquinone; Diarylethene; Mallory reaction; Photocyclization; Reduction

Authors

Sergeeva Ekaterina S. ^1,2 , Migulin Vasily A. ² , Ushakov Igor A. ¹ , Faizdrakhmanova Anna A. ^1,3 , Antsiferov Evgenii A. ³ , Lvov Andrey G. ^1,3

Affiliations

1	A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russia
2	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47, Leninsky prospect, Moscow, Russia
3	Irkutsk National Research Technical University, 83, Lermontov St., Irkutsk 664074, Russia

The oxidative photocyclization of 1,2-diarylethenes to phenanthrenes or their isoelectronic analogues (Mallory reaction) has been tested on a wide range of substrates; however, 1,4-naphthoquinone derivatives have not previously been involved in this reaction. In this work, the photoactivity of various symmetric 2,3-di(het)arylsubstituted naphthoquinones was probed for the first time. It was found that thiophene derivatives are photoactive and demonstrate the formation of Mallory products upon irradiation in an oxygen environment. Photolysis of these naphthoquinones in an inert atmosphere revealed the occurrence of a redox process leading to the formation of naphthalene-1,4-diol paired with the Mallory product.

Sergeeva E.S. , Migulin V.A. , Ushakov I.A. , Faizdrakhmanova A.A. , Antsiferov E.A. , Lvov A.G.
A trick of the Mallory reaction of 2,3-diaryl-substituted naphthoquinones: a primary photoproduct as a reductant
Journal of Photochemistry and Photobiology A: Chemistry. 2026. V.477. 117113 :1-5. DOI: 10.1016/j.jphotochem.2026.117113 Scopus OpenAlex

Submitted:	Oct 16, 2025
Accepted:	Feb 11, 2026
Published online:	Feb 14, 2026

Scopus:	2-s2.0-105030882131
OpenAlex:	W7128913160

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