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Synthesis of 8-Aza- and 8,8′-Diaza-BINOL Derivatives through Cu(II)-TMEDA-Catalyzed Aerobic Oxidative Coupling

Year: 2025

Type: article

Abstract: A practical Cu(II)-TMEDA-catalyzed oxidative coupling of 7-hydroxyquinoline was developed with air as an oxidant, affording 8-aza- and 8,8'-diaza-BINOL derivatives in moderate to good yields. In addition, a series of post-transformations further demonstrated the utility of the current process, especially for the synthesis of novel hetero[5]helicenes with unique fluorescence properties.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.5c01897

Authors: Guishun Bai, Ruoqi Liu, Yang Yang, Damien Bonne, Jean Rodriguez, Shi-Qiang Wei, Hong Wang, Xiaoze Bao

Institutions: Zhejiang University of Technology, Centre National de la Recherche Scientifique, Aix-Marseille Université, Centrale Méditerranée, Institut des Sciences Moléculaires de Marseille, Shanghai Jiao Tong University

Language: English

Topic: Axial and Atropisomeric Chirality Synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Natural Science Foundation of Shanghai, National Natural Science Foundation of China, National Key Research and Development Program of China

Awards: G1031941127, G5134441095, G6614432331

OpenAlex ID: W4417311697

FWCI:

Cites: 52

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