Photoredox-catalyzed intramolecular cyclopropanation of alkenes with α-bromo-β-keto esters
Photoredox-catalyzed intramolecular cyclopropanation of alkenes with α-bromo-β-keto esters
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DOI：
10.1039/d1ob01733k
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发表时间：
2021-10-09
影响因子：
3.2
通讯作者：
Tokuyama, Hidetoshi
中科院分区：
文献类型：
--
作者：
Ide, Kohta;Furuta, Miyu;Tokuyama, Hidetoshi
研究了一种温和的光氧化催化烯烃与-溴- -酮酯在水介质中的分子内环丙烷化反应。在2,6-lutidine的存在下，在室温下，在异常温和的条件下，在一个锅中进行了一系列的反应过程，包括在光氧化还原催化下将α -溴- β -酮酯分子内自由基加成到烯烃，然后环合形成环丙烷。在反应条件下，由各种烯烃和碱敏和酸敏官能化酯组成的广泛底物是可行的，从而得到广泛的官能化双环丙烷。
A mild photoredox-catalyzed intramolecular cyclopropanation of alkenes with alpha-bromo-beta-keto esters in an aqueous medium was developed. The sequential reaction process comprising the intramolecular radical addition of alpha-bromo-beta-keto esters to olefins under photoredox catalysis, and subsequent cyclization to form cyclopropane proceeds in one-pot under exceptionally mild conditions at room temperature in the presence of 2,6-lutidine. A broad range of substrates consisting of various alkenes and both base- and acid-sensitive functionalized esters were feasible under the reaction conditions, resulting in a wide range of functionalized bicyclic cyclopropanes.