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New catalytic effect of thiourea on the oxidative cyanation of N-aryltetrahydroisoquinolines
Tetrahedron Letters ( IF 1.8 ) Pub Date : 2018-12-22 , DOI: 10.1016/j.tetlet.2018.12.050
Bakhtar Ullah , Yuli Zhou , Jingwen Chen , Zongbi Bao , Yiwen Yang , Qiwei Yang , Qilong Ren , Zhiguo Zhang

Thiourea itself has been introduced as a mild and efficient organocatalyst for the oxidative α -cyanation of N-aryltetrahydroisoquinolines (THIQs) with trimethylsilyl cyanide (TMSCN), giving the corresponding products in good to excellent yields. Experimental investigations demonstrated that thiourea acts as a radical initiator by abstracting hydroxyl radical (OH) from tert-butyl hydroperoxide (TBHP) directly instead of non-covalent hydrogen bondings (H-bondings) activation. The use of thiourea as a radical initiator offers a new avenue for innovative chemical transformations in organocatalyzed radical chemistry.



中文翻译:

硫脲对N-四氢异喹啉氧化氰化的新催化作用

硫脲本身已被引入作为温和有效的有机催化剂,用于将N-芳基四氢异喹啉(THIQs)与三甲基甲硅烷基氰化物(TMSCN)进行氧化性α-氰化反应,从而使相应的产品收率良好至优异。实验研究表明,硫脲通过直接丁基过氧化氢(TBHP)中提取羟基(OH)而不是非共价氢键(H-bondings)活化来充当自由基引发剂。硫脲作为自由基引发剂的使用为有机催化自由基化学中的创新化学转化提供了新途径。

更新日期:2018-12-22
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