Divergent Synthesis of Tetrasubstituted Phenols via [3 + 3] Cycloaddition Reaction of Vinyl Sulfoxonnium Ylides with Cyclopropenones.
Divergent Synthesis of Tetrasubstituted Phenols via [3 + 3] Cycloaddition Reaction of Vinyl Sulfoxonnium Ylides with Cyclopropenones.
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DOI：
10.1021/acs.orglett.3c01327
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发表时间：
2023-06
期刊：
影响因子：
5.2
通讯作者：
Shaojun Chen;Yao‐Fu Zeng;Wenlong Zou;Dan-Ting Shen;Yi-Chuan Zheng;Jia-lin Song;Shang‐Shi Zhang
中科院分区：
文献类型：
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作者：
Shaojun Chen;Yao‐Fu Zeng;Wenlong Zou;Dan-Ting Shen;Yi-Chuan Zheng;Jia-lin Song;Shang‐Shi Zhang
通过乙烯基亚砜基叶立德与环丙烯酮的环加成反应，以可切换的方式合成了两类四取代苯酚。2，3，4，5-四取代苯酚的生成过程中，类卡宾铜可能是活性中间体，而2，3，5，6-四取代苯酚则是通过乙烯基亚砜与环丙烯酮在无金属条件下直接[3 + 3]成环反应生成的。还展示了进一步的合成应用。
Two categories of tetrasubstituted phenols were prepared via the cycloaddition reaction of vinyl sulfoxonnium ylides with cyclopropenones in a switchable manner. Copper carbenoid was proposed as the active intermediate in the process of 2,3,4,5-tetrasubstituted phenols formation, while 2,3,5,6-tetrasubstituted phenols were generated via the direct [3 + 3] annulation of vinyl sulfoxonnium ylides with cyclopropenones under metal-free conditions. Further synthetic applications were also demonstrated.