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New catalytic effect of thiourea on the oxidative cyanation of N-aryltetrahydroisoquinolines
Authors:Bakhtar Ullah  Yuli Zhou  Jingwen Chen  Zongbi Bao  Yiwen Yang  Qiwei Yang  Qilong Ren  Zhiguo Zhang
Institution:Key Laboratory of Biomass Chemical Engineering of Ministry of Education, College of Chemical and Biological Engineering, Zhejiang University, Zheda Road 38, Hangzhou 310027, China
Abstract: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 <em>tert</em>-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.</td>
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Keywords:α-Aminonitriles  Cyanation  Organocatalysis  Thiourea
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