Radical Cation Cycloadditions Using Cleavable Redox Auxiliaries.
Radical Cation Cycloadditions Using Cleavable Redox Auxiliaries.
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DOI：
10.1021/acs.orglett.6b03545
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发表时间：
2017-01-20
期刊：
影响因子：
5.2
通讯作者：
Yoon TP
中科院分区：
文献类型：
--
作者：
Lin S;Lies SD;Gravatt CS;Yoon TP
容易氧化的芳基硫醚部分的掺入促进烯烃自由基阳离子的光催化生成，所述烯烃自由基阳离子与富电子反应伙伴进行各种环加成反应。硫化物部分随后可以以无痕方式还原裂解，从而提供使用光氧化还原催化不能直接获得的产物。这种方法构成了一种新的氧化“氧化还原辅助”的策略，提供了一种实用的手段，以规避面临的光氧化还原反应的基本热力学限制。
The incorporation of an easily oxidized arylsulfide moiety facilitates the photocatalytic generation of alkene radical cations that undergo a variety of cycloaddition reactions with electron-rich reaction partners. The sulfide moiety can subsequently be reductively cleaved in a traceless fashion, affording products that are not otherwise directly accessible using photoredox catalysis. This approach constitutes a novel oxidative “redox auxiliary” strategy that offers a practical means to circumvent a fundamental thermodynamic limitation facing photoredox reactions.