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

Author:
Ullah, Bakhtar, Zhou, Yuli, Chen, Jingwen, Bao, Zongbi, Yang, Yiwen, Yang, Qiwei, Ren, Qilong, Zhang, Zhiguo
Source:
Tetrahedron letters 2019 v.60 no.4 pp. 348-351
ISSN:
0040-4039
Subject:
chemical reactions, chemical structure, cyanides, hydrogen bonding, hydroxyl radicals, organocatalysts, thiourea
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 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.
Agid:
6290006