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Visible Light-Mediated Co(II) Catalyzed Synthesis of α,β-Epoxy Ketones by Oxidative Coupling of Alkenes and Aldehydes in Water
Organic Letters ( IF 4.9 ) Pub Date : 2024-09-17 , DOI: 10.1021/acs.orglett.4c03098
Adwitiya Pal 1 , Bijan Mondal 2 , Subham Sau 1 , Soumita De 1 , Arunabha Thakur 1
Affiliation  

A one-step, two-component visible light-mediated CoCl2·6H2O-catalyzed oxidative acylation of alkenes by aldehydes to synthesize α,β-epoxy ketone has been achieved in water at room temperature. The photocatalytic activity of Co(II) presented a remarkable achievement for synthesis of α,β-epoxy ketones from aldehydes and olefins, with a wide substrate compatibility including aromatic, heteroaromatic and aliphatic aldehydes, styrenes with both electron-donating and withdrawing groups, α-substituted styrenes, stilbene, acrylates, and even the challenging unactivated aliphatic alkenes. Mechanistic studies including radical trapping experiments, intermediate detection by GCMS, Hammett analysis, and DFT studies unveil the nature of the photocatalytic pathway.

中文翻译:


可见光介导的 Co(II) 催化烯烃和醛在水中氧化偶联合成 α,β-环氧酮



室温下在水中实现了一步、二组分可见光介导的CoCl 2 ·6H 2 O催化醛与烯烃的氧化酰化合成α,β-环氧酮。 Co(II)的光催化活性在醛和烯烃合成α,β-环氧酮方面取得了显着的成就,具有广泛的底物兼容性,包括芳香族、杂芳香族和脂肪族醛、具有给电子基团和吸电子基团的苯乙烯、α -取代的苯乙烯、二苯乙烯、丙烯酸酯,甚至是具有挑战性的未活化脂肪族烯烃。包括自由基捕获实验、GCMS 中间检测、Hammett 分析和 DFT 研究在内的机理研究揭示了光催化途径的本质。
更新日期:2024-09-17
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