1582284-65-8Relevant academic research and scientific papers
Efficient and General Aerobic Oxidative Cross-Coupling of THIQs with Organozinc Reagents Catalyzed by CuCl2: Proof of a Radical Intermediate
Wang, Tongtong,Schrempp, Michael,Berndh?user, Andreas,Schiemann, Olav,Menche, Dirk
, p. 3982 - 3985 (2015)
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 sp3 C-H bond activation allowing for an sp3-sp3 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.
Direct sp3 C-H bond arylation, alkylation, and amidation of tetrahydroisoquinolines mediated by hypervalent iodine(iii) under mild conditions
Muramatsu, Wataru,Nakano, Kimihiro,Li, Chao-Jun
supporting information, p. 2189 - 2192 (2014/04/03)
We have developed a method for the sp3 C-H bond functionalization of tetrahydroisoquinolines (THIQs) mediated by [bis(trifluoroacetoxy)iodo]benzene (PIFA). The treatment of the THIQs with various nucleophiles in the presence of PIFA in a green solvent alternative gave the coupled products, with a C-C, C-N, or quaternary carbon center in high yields. This journal is
