New catalytic effect of thiourea on the oxidative cyanation of N-aryltetrahydroisoquinolines

New catalytic effect of thiourea on the oxidative cyanation of N-aryltetrahydroisoquinolines
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硫脲对N-芳基四氢异喹啉氧化氰化的新催化作用

DOI:
10.1016/j.tetlet.2018.12.050
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发表时间:
2019-01
影响因子:
1.8
通讯作者:
Zhang Zhiguo
Zhang Zhiguo
中科院分区:
化学4区
文献类型:
--
作者:
Ullah Bakhtar;Zhou Yuli;Chen Jingwen;Bao Zongbi;Yang Yiwen;Yang Qiwei;Ren Qilong;Zhang Zhiguo

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噻托溴铵本身已被引入作为一种温和而有效的有机催化剂,用于N-芳基四氢异喹啉(THIQs)与三甲基硅烷氰化物(TMSCN)的氧化α-氰化反应,以良好到优异的产率得到相应的产物。实验研究表明,硫脲作为自由基引发剂是通过直接从叔丁基过氧化氢(TBHP)中夺取羟基自由基(中心点OH)而不是通过非共价氢键(H-键)活化。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的途径。(C)2018爱思唯尔有限公司版权所有。
Thiourea itself has been introduced as a mild and efficient organocatalyst for the oxidative alpha-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 (center dot 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. (C) 2018 Elsevier Ltd. All rights reserved.
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