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Efficiently Constructing Tetrahydroquinolines through Cascade Radical Additions and Cyclizations under the Catalysis of Cu I
Author(s) -
Zhou Weiyou,
Tian Xiaoting,
Zhen Yingxing,
Wang Anwei,
He Mingyang,
Sun Shixin
Publication year - 2021
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202101928
Subject(s) - chemistry , catalysis , radical , radical cyclization , cascade reaction , copper , reaction intermediate , cascade , combinatorial chemistry , photochemistry , medicinal chemistry , organic chemistry , chromatography
An efficient method has been developed for the construction of tetrahydroquinolines from N , N ‐dimethylanilines and electron‐deficient alkenes based on CuCl/O 2 . A wide scope of substrates could be well tolerated, and excellent yields of the products were obtained. A series of control experiments and kinetic isotope effect experiments have been performed to gain insight of the catalytic reaction pathway. The reaction is probably initiated by the reaction of Cu I and molecular oxygen to give copper(II) superoxide (Cu II OO . ) as the key reactive intermediate. The formed Cu II OO . species can directly abstract a hydrogen from the α ‐site of nitrogen to give the α ‐amino radical intermediate, which then finishes the transformation via radical addition and cyclization.