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

Autor:	Dirk Menche, Olav Schiemann, Tongtong Wang, Andreas Berndhäuser, Michael Schrempp
Rok vydání:	2015
Předmět:	Chemistry Organic Chemistry Regioselectivity Iminium Oxidative phosphorylation Biochemistry Combinatorial chemistry law.invention Catalysis Coupling (electronics) law Reagent THIQ medicine Organic chemistry Physical and Theoretical Chemistry Electron paramagnetic resonance medicine.drug
Zdroj:	Organic Letters. 17:3982-3985
ISSN:	1523-7052 1523-7060
DOI:	10.1021/acs.orglett.5b01845
Popis:	A general new method for the highly concise synthesis of C-1-alkylated tetrahydroisoquinolines (THIQ) is reported. The CuCl2-catalyzed procedure is based on a coupling of nonfunctionalized THIQs with organozinc reagents under aerobic conditions. It proceeds in high yields and is broadly applicable to a wide range of substrates. It relies on a regioselective sp(3) C-H bond activation allowing for an sp(3)-sp(3) bond union under mild reaction conditions in a rapid and effective manner. Mechanistically it involves an iminium ion intermediate that is formed via an organic radical involving a single-electron-transfer process. For the first time for this type of reaction a radical intermediate has been proven by EPR spectroscopy.
Databáze:	OpenAIRE
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