可见光诱导的 2-溴-1,3-二羰基化合物和炔烃的分子间去芳构化环化反应：螺[4.5]癸-1,6,9-三烯-8-酮的合成。
Visible-Light-Induced Intermolecular Dearomative Cyclization of 2-Bromo-1,3-dicarbonyl Compounds and Alkynes: Synthesis of Spiro[4.5]deca-1,6,9-trien-8-ones.
机构信息
Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering , Shanghai Jiao Tong University , 800 Dongchuan Road , Shanghai 200240 , China.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry , Chinese Academy of Sciences , 345 Lingling Road , Shanghai 200032 , China.
出版信息
Org Lett. 2018 Sep 21;20(18):5762-5765. doi: 10.1021/acs.orglett.8b02463. Epub 2018 Sep 7.
A visible-light-induced photocatalytic intermolecular dearomative cyclization of 2-bromo-1,3-dicarbonyl compounds and alkynes afforded biologically important spirocarbocycle structures in moderate to good yields via a 5-exo-dig radical cyclization under mild reaction conditions. A 5.0 mmol scale dearomatization reaction proceeded smoothly with 95% yield even when the catalyst loading was reduced to 0.1 mol %, suggesting that this method was suitable for large-scale synthesis.
可见光诱导的 2-溴-1,3-二羰基化合物和炔烃的分子间去芳构化光催化环化反应，在温和的反应条件下，通过 5-endo-dig 自由基环化，以中等至良好的收率提供了具有重要生物意义的螺环碳环结构。即使催化剂负载量降低至 0.1mol%，5.0mmol 规模的去芳构化反应仍能顺利进行，收率为 95%，这表明该方法适用于大规模合成。
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