Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 17, Pages 6775-6779Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202000585
Keywords
amination; atropisomerism; chiral phosphoric acid; heterocycles; organocatalysis
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Funding
- National Natural Science Foundation of China [21772081, 21825105, 21702092, 21901105]
- Shenzhen Nobel Prize Scientists Laboratory Project [C17213101]
- Shenzhen Special Funds for the Development of Biomedicine, Internet, New Energy, and New Material Industries [JCYJ20170412151701379]
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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.
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