化学
电化学
组合化学
反应性(心理学)
氧化还原
级联
自由基环化
级联反应
电子转移
有机合成
有机化学
还原(数学)
激进的
自由基离子
四氢萘酮
分解
作者
H C Sun,Feng Tan,Jingyi Ruan,Y S Yang,Hu Tan,Gulixiayida Wumaier,Hui Zhou,Dong Zhang,Qianwen He
标识
DOI:10.1021/acs.joc.6c01095
摘要
Herein, we report an electrochemical cascade cyclization of sulfoxonium ylides with unactivated alkenes under mild conditions. This protocol provides a concise and sustainable route to γ-substituted 1-tetralones. Mechanistically, this oxidant- and metal-free transformation proceeds via the generation of an α-carbonyl carbon radical through the reductive proton-coupled electron transfer of sulfoxonium ylides at the cathode, which subsequently triggers a radical addition/cascade cyclization sequence with unactivated alkenes. The success of this reaction relies on the precise matching of redox potentials to facilitate both the initiation of the reduction and the subsequent oxidation of the key radical intermediate to complete the cycle. This work not only provides a practical and complementary synthetic strategy for the construction of valuable tetralone scaffolds but also expands the reactivity landscape of sulfoxonium ylides in catalyst-free electrochemical radical chemistry.
科研通智能强力驱动
Strongly Powered by AbleSci AI