N‐Hydroxyphthalimide/TiO2 Catalyzed Addition of Ethers, Alkylarenes and Aldehydes to Azodicarboxylates under Visible Light

N‐Hydroxyphthalimide/TiO2 Catalyzed Addition of Ethers, Alkylarenes and Aldehydes to Azodicarboxylates under Visible Light Full article

Journal

Chemistry: A European Journal
ISSN: 0947-6539 , E-ISSN: 1521-3765

Output data

Year: 2025, Volume: 31, Number: 17, Article number : e202404687, Pages count : DOI: 10.1002/chem.202404687

Authors

Lopat'eva Elena R. ¹ , Krylov Igor B. ¹ , Terent'ev Alexander O. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation

The addition of carbon-centered radicals to double bonds is one of the most atom-efficient approaches to the formation of new C−C or C−heteroatom bonds. Existing approaches for the generation of carbon-centered radicals often require elevated temperatures, UV radiation or expensive transition metal catalysts. In this work, a photocatalytic system based on a heterogeneous TiO2 catalyst and a redox organocatalyst N-hydroxyphthalimide is proposed for the generation of carbon-centered radicals from C(sp3)−H substrates or aldehydes at room temperature under visible light irradiation. The developed approach was successfully applied to the addition of ethers, alkylarenes and aldehydes to azodicarboxylates. Titanium oxide acts as a photocatalyst, producing phthalimide-N-oxyl radicals from N-hydroxyphthalimide, thereby enabling the organocatalytic process in solution. Phthalimide-N-oxyl radicals act as catalytically active species that cleave C−H bonds to form carbon-centered radicals.

Lopat'eva E.R. , Krylov I.B. , Terent'ev A.O.
N‐Hydroxyphthalimide/TiO2 Catalyzed Addition of Ethers, Alkylarenes and Aldehydes to Azodicarboxylates under Visible Light
Chemistry: A European Journal. 2025. V.31. N17. e202404687 . DOI: 10.1002/chem.202404687 WOS OpenAlex

Web of science:	WOS:001426789100001
OpenAlex:	W4407028375

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