Efficient and General Aerobic Oxidative Cross-Coupling of THIQs with Organozinc Reagents Catalyzed by CuCl2: Proof of a Radical Intermediate.
作者： Tongtong Wang , Michael Schrempp , Andreas Berndhäuser , Olav Schiemann , Dirk Menche
DOI: 10.1021/ACS.ORGLETT.5B01845
关键词:
摘要: A general new method for the highly concise synthesis of C-1-alkylated tetrahydroisoquinolines (THIQ) is reported. The CuCl2-catalyzed procedure based on a coupling nonfunctionalized THIQs with organozinc reagents under aerobic conditions. It proceeds in high yields and broadly applicable to wide range substrates. relies regioselective sp3 C–H bond activation allowing an sp3–sp3 union mild reaction conditions rapid effective manner. Mechanistically it involves iminium ion intermediate that formed via organic radical involving single-electron-transfer process. For first time this type has been proven by EPR spectroscopy.
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