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Efficient and General Aerobic Oxidative Cross-Coupling of THIQs with Organozinc Reagents Catalyzed by CuCl2: Proof of a Radical Intermediate

Tongtong Wang, Michael Schrempp, Andreas Berndhäuser, Olav Schiemann and Dirk Menche*

*Kekulé-Intitute of Organic Chemistry and Biochemistry, University of Bonn, Gerhard-Domagk-Strasse 1, D-53121 Bonn, Germany, Email: dirk.mencheuni-bonn.de

T. Wang, M. Schrempp, A. Berndhäuser, O. Schiemann, D. Menche, Org. Lett., 2015, 17, 3982-3985.

DOI: 10.1021/acs.orglett.5b01845 (free Supporting Information)


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Abstract

An efficient CuCl2-catalyzed coupling of nonfunctionalized tetrahydroisoquinolines with organozinc reagents under aerobic conditions proceeds in high yields under mild reaction conditions and is broadly applicable to a wide range of substrates. The reaction involves an iminium ion intermediate that is formed via a SET process.

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Key Words

tetrahydroisoquinolines, oxygen


ID: J54-Y2015