Formal insertion of selenoketenes into donor–acceptor cyclopropanes: mesomeric alkynylselenolates as key starting materials,Organic Chemistry Frontiers

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Formal insertion of selenoketenes into donor–acceptor cyclopropanes: mesomeric alkynylselenolates as key starting materials
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2022-11-07 , DOI: 10.1039/d2qo01568d
Anu Jacob ₁ , Peter G. Jones ₂ , Daniel B. Werz ₃

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Donor–acceptor cyclopropanes (DACs) react with lithium alkynylselenolates in the presence of In(OTf)₃ to furnish tetrahydroselenophenes with exocyclic double bonds. The reaction can be regarded as a formal insertion of selenoketenes into the strained three-membered ring systems. Lithium alkynylselenolates are generated in situ from lithium acetylides and elemental selenium. The reactions afford tetrahydroselenophenes with a broad substrate scope and high yields (up to 95%).

中文翻译：

硒烯烯正式插入供体-受体环丙烷：中间体炔基硒化物作为关键起始材料

_{在 In(OTf) 3}存在下，供体-受体环丙烷 (DAC) 与锂炔基硒化物反应生成具有环外双键的四氢硒酚。该反应可以被视为将硒烯酮正式插入到应变三元环系统中。锂炔基硒化物由乙炔锂和元素硒原位生成。该反应提供了具有广泛底物范围和高产率（高达 95%）的四氢硒酚。

更新日期：2022-11-10

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