New catalytic effect of thiourea on the oxidative cyanation of N-aryltetrahydroisoquinolines
2019
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.
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