Regioselective Neighboring-Group-Participated 2,4-Dibromohydration of Conjugated Enynes: Synthesis of 2-(2,4-Dibromobut-2-enoyl)benzoate and Its Applications,Organic Letters

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Regioselective Neighboring-Group-Participated 2,4-Dibromohydration of Conjugated Enynes: Synthesis of 2-(2,4-Dibromobut-2-enoyl)benzoate and Its Applications
Organic Letters ( IF 4.9 ) Pub Date : 2018-01-11 00:00:00 , DOI: 10.1021/acs.orglett.7b03671
Si-Tian Yuan _{1,

2} , Hongwei Zhou ₁ , Liang Gao ₃ , Jin-Biao Liu ₂ , Guanyinsheng Qiu ₁

Affiliation

A regioselective 2,4-dibromohydration of conjugated enynes is reported for the synthesis of 2-(2,4-dibromobut-2-enoyl)benzoate. In the presence of tetra-n-butylammonium bromide and H₂O the transformation proceeds smoothly with good reaction efficiency and a broad reaction scope. Mechanism studies indicate that the neighboring ester group participates in the 2,4-dibromohydration, and the oxygen atom of ester is transferred into the C–C triple bond to form the keto carbonyl group in the product. 2-(2,4-Dibromobut-2-enoyl)benzoate is recognized as an important synthon toward phthalazin-1(2H)-one and the natural product Shihunine.

中文翻译：

区域选择性的邻域参与的共轭炔烃的2,4-二溴水合反应：2-（2,4-二溴丁-2-烯酰基）苯甲酸酯的合成及其应用

据报道，共轭烯炔的区域选择性的2,4-二溴水合用于合成2-（2,4-二溴丁-2-烯酰基）苯甲酸酯。在溴化四正丁基铵和H ₂ O的存在下，转化顺利进行，反应效率高，反应范围广。机理研究表明，相邻的酯基团参与了2,4-二溴水合反应，酯的氧原子被转移到C-C三键中，从而在产物中形成酮羰基。2-（2,4-二溴丁-2-烯酰基）苯甲酸酯被认为是酞菁-1（2 H）-one和天然产物Shihunine的重要合成子。

更新日期：2018-01-11

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