Investigating the Oxidation Step in the CuCl2-Catalyzed Aerobic Oxidative Coupling Reaction of N-Aryl Tetrahydroisoquinolines | Zendy

Esther Boess | Zendy; Max Van Hoof | Zendy; Sarah Luna Birdsall | Zendy; Martin Klußmann | Zendy

Open Access

Investigating the Oxidation Step in the CuCl₂-Catalyzed Aerobic Oxidative Coupling Reaction of N-Aryl Tetrahydroisoquinolines

Author(s) -

Esther Boess,

Max Van Hoof,

Sarah Luna Birdsall,

Martin Klußmann

Publication year - 2019

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.9b02707

Subject(s) - chemistry , iminium , aryl , nucleophile , catalysis , oxidative coupling of methane , amine gas treating , substrate (aquarium) , oxidative phosphorylation , combinatorial chemistry , photochemistry , organic chemistry , medicinal chemistry , biochemistry , alkyl , oceanography , geology

The oxidative coupling of N -aryl tetrahydroisoquinolines with nucleophiles has inspired the development of novel C-H functionalization reactions as well as mechanistic studies. Here, we investigate the oxidation step that forms iminium ions as key intermediates in the method using CuCl 2 as the catalyst and oxygen as the terminal oxidant. A strong electronic effect of substituents in the N-aryl ring was found by synthetic studies and a Hammett plot analysis, supporting initial electron transfer from the amine to Cu(II). The importance of the mechanism of oxidation on the substrate scope with differently substituted tetrahydroisoquinolines is discussed.

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