Stereoselective Synthesis of Cyclohepta[b]indoles by Visible-Light-Induced [2+2]-Cycloaddition/retro-Mannich-type Reactions
Stereoselective Synthesis of Cyclohepta[b]indoles by Visible-Light-Induced [2+2]-Cycloaddition/retro-Mannich-type Reactions
复制标题
可见光诱导[2 2]-环加成/逆曼尼希型反应立体选择性合成环庚[b]吲哚
DOI：
10.1002/anie.202101104
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发表时间：
2021-04-07
影响因子：
16.6
通讯作者：
Yang, Zhen
中科院分区：
文献类型：
--
作者：
Mu, Xin-Peng;Li, Yuan-He;Yang, Zhen
发展了一种简便、高产率合成环庚并[B]吲哚的新方法。该方法涉及烯胺酮的可见光诱导的光催化[2+2]-环加成/逆Mannich型反应。实验和计算研究表明，该反应是一个光氧化还原过程开始由单电子氧化的烯胺酮部分，它经历了随后的环丁烷的形成和快速断裂的自由基阳离子状态，形成环庚[B]吲哚。
A novel method for the concise synthesis of cyclohepta[b]indoles in high yields was developed. The method involves a visible-light-induced, photocatalyzed [2+2]-cycloaddition/ retro-Mannich-type reaction of enaminones. Experimental and computational studies suggested that the reaction is a photoredox process initiated by single-electron oxidation of an enaminone moiety, which undergoes subsequent cyclobutane formation and rapidly fragmentation in a radical-cation state to form cyclohepta[b]indoles.