Decatungstate-photoinitiated skeletal editing of cyclic ketones by ring expansion/acylation

Decatungstate-photoinitiated skeletal editing of cyclic ketones by ring expansion/acylation Full article

Journal

Science China Chemistry
ISSN: 1869-1870 , E-ISSN: 1674-7291

Output data

Year: 2025, Volume: 69, Number: 1, Pages: 347-353 Pages count : 7 DOI: 10.1007/s11426-025-2812-3

Authors

Qiao Lipeng ¹ , Yang Wumeng ^1,2 , Li Xingyu ¹ , Sun Kai ¹ , Liu Yan ³ , Chen Xiaolan ¹ , Krylov Igor B. ⁴ , Liu Peng ⁵ , Qu Lingbo ^1,5 , Terent’ev Alexander O. ⁴ , Yu Bing ¹

Affiliations

1	College of Chemistry, Henan Joint International Research Laboratory of Green Construction of Functional Molecules and Their Bioanalytical Applications, Zhengzhou University, Zhengzhou, 450001, China
2	National Engineering Research Center of Low-Carbon Processing and Utilization of Forest Biomass, Nanjing Forestry University, Nanjing, 210037, China
3	Henan International Joint Laboratory of Rare Earth Composite Material, College of Materials Engineering, Henan University of Engineering, Zhengzhou, 451191, China
4	N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Moscow, 119991, Russia
5	Institute of Chemistry, Henan Academy of Sciences (ICHAS), Zhengzhou, 450002, China

Six-membered and seven-membered carbocycles are prevalent in nature due to their low ring strain and structural stability. In this work, we introduce a novel photocatalytic skeletal editing strategy for Dowd-Beckwith ring expansion acylation, leveraging tetrabutylammonium decatungstate (TBADT) as a hydrogen atom transfer (HAT) photocatalyst. This innovative approach enables the efficient synthesis of a diverse range of six- and seven-membered cyclic ketones under mild conditions, offering key advantages including environmental sustainability, high atom and step economy, good functional group tolerance, and the potential for extensive downstream functionalization. The versatility of this strategy is further demonstrated by its successful application in the post-synthetic modification of complex pharmaceutical intermediates and its scalability via continuous-flow technology, underscoring its broad utility in synthetic chemistry and pharmaceutical development.

Qiao L. , Yang W. , Li X. , Sun K. , Liu Y. , Chen X. , Krylov I.B. , Liu P. , Qu L. , Terent’ev A.O. , Yu B.
Decatungstate-photoinitiated skeletal editing of cyclic ketones by ring expansion/acylation
Science China Chemistry. 2025. V.69. N1. P.347-353. DOI: 10.1007/s11426-025-2812-3 WOS Scopus OpenAlex

Web of science:	WOS:001558762300001
Scopus:	2-s2.0-105014273794
OpenAlex:	W4413767382

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