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Chiral Phosphoric Acid Catalyzed Atroposelective C−H Amination of Arenes
Author(s) -
Xia Wang,
An QianJin,
Xiang ShaoHua,
Li Shaoyu,
Wang YongBin,
Tan Bin
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202000585
Subject(s) - amination , atropisomer , enantioselective synthesis , combinatorial chemistry , chemistry , catalysis , aryl , organocatalysis , substrate (aquarium) , organic chemistry , alkyl , oceanography , geology
Abstract N‐arylcarbazole structures are important because of their prevalence in natural products and functional OLED materials. C−H amination of arenes has been widely recognized as the most efficient approach to access these structures. Conventional strategies involving transition‐metal catalysts suffer from confined substrate generality and the requirement of exogenous oxidants. Organocatalytic enantioselective C–N chiral axis construction remains elusive. Presented here is the first organocatalytic strategy for the synthesis of novel axially chiral N‐arylcarbazole frameworks by the assembly of azonaphthalenes and carbazoles. This reaction accommodates broad substrate scope and gives atropisomeric N‐arylcarbazoles in good yields with excellent enantiocontrol. This approach not only offers an alternative to metal‐catalyzed C–N cross‐coupling, but also brings about opportunities for the exploitation of structurally diverse N‐aryl atropisomers and OLED materials.