Silver-Catalyzed Radical Umpolung Cross-Coupling of Silyl Enol Ethers with Activated Methylene Compounds: Access to Diverse Tricarbonyl Derivatives.

Tongwei Liang, Qingjia Yuan, Li Xu, Jian-Quan Liu, Markus D Kärkäs, Xiang-Shan Wang

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Article in The Journal of organic chemistry, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

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1citing papers in PubMed

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1 citing paper in PubMed.

Catalytic Enantioselective Cross-Nucleophile Coupling via Valence Tautomerism.Journal of the American Chemical Society · 2025
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6 authors.

Tongwei LiangSchool of Chemistry and Materials Science, Jiangsu Key Laboratory of Green Synthesis for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 221116, China.

Qingjia YuanSchool of Chemistry and Materials Science, Jiangsu Key Laboratory of Green Synthesis for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 221116, China.

Li XuSchool of Chemistry and Materials Science, Jiangsu Key Laboratory of Green Synthesis for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 221116, China.

Jian-Quan LiuSchool of Chemistry and Materials Science, Jiangsu Key Laboratory of Green Synthesis for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 221116, China.ORCID 0000-0002-5533-2075

Markus D KärkäsDepartment of Chemistry, KTH Royal Institute of Technology, SE-100 44 Stockholm, Sweden.ORCID 0000-0002-6089-5454

Xiang-Shan WangSchool of Chemistry and Materials Science, Jiangsu Key Laboratory of Green Synthesis for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 221116, China.

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

A silver-catalyzed protocol for the intermolecular radical umpolung cross-coupling protocol of silyl enol ethers with activated methylene compounds is disclosed. The protocol exhibits excellent functional group tolerance, enabling the expedient preparation of a variety of tricarbonyl compounds. Preliminary mechanistic investigations suggest that the reaction proceeds through a process involving free radicals in which silver oxide has a dual role, acting as both a catalyst and a base.

Identifiers

PMID38877984

DOI10.1021/acs.joc.4c00310

PMCPMC11232002

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