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Photocatalytic Generation of Carbocation from Thiols and Application to Cross-Nucleophile Coupling
Organic Letters ( IF 5.2 ) Pub Date : 2024-05-09 , DOI: 10.1021/acs.orglett.4c01261
Ge Liang 1, 2 , Shu Wang 1, 2 , Chao Zhou 1, 2 , Chen Ye 1, 2 , Bin Chen 1, 2 , Chen-Ho Tung 1, 2 , Li-Zhu Wu 1, 2
Affiliation  

Represented herein is a simple thiol identified as an effective precursor to photochemically form a carbocation. Thanks to the thiyl radical rapid transformation to disulfide, which serves not only to stabilize the generated thiyl radical but also to allow the second electron transfer to form a carbocation. The resulting carbocations, including primary benzylic, secondary, and tertiary carbocations, can smoothly couple with nitrogen, oxygen, and carbon nucleophilic coupling partners as well as complex drug molecules, accompanied by elemental sulfur formation in air.

中文翻译:


硫醇光催化生成碳正离子及其在交叉亲核偶联中的应用



本文代表的是一种简单的硫醇,被鉴定为光化学形成碳正离子的有效前体。由于硫基自由基快速转化为二硫化物,这不仅可以稳定生成的硫基自由基,还可以允许第二次电子转移形成碳正离子。所得的碳阳离子,包括伯苄基、仲碳和叔碳阳离子,可以与氮、氧和碳亲核偶联伙伴以及复杂的药物分子顺利偶联,同时在空气中形成元素硫。
更新日期:2024-05-09
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