A Highly Selective Palladium-Catalyzed Aerobic Oxidative Aniline–Aniline Cross-Coupling Reaction

The first catalytic oxidative aniline–aniline cross-coupling reaction using oxygen as the terminal oxidant is reported. Anilines possessing a pyrrolidino group can be preferentially oxidized under mild aerobic conditions and reacted with other anilines to afford a variety of nonsymmetrical 2-aminobi...

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Bibliographic Details
Published in:Organic letters 2019-09, Vol.21 (18), p.7279-7283
Main Authors: Matsumoto, Kenji, Takeda, Satoshi, Hirokane, Tsukasa, Yoshida, Masahiro
Format: Article
Language:English
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Summary:The first catalytic oxidative aniline–aniline cross-coupling reaction using oxygen as the terminal oxidant is reported. Anilines possessing a pyrrolidino group can be preferentially oxidized under mild aerobic conditions and reacted with other anilines to afford a variety of nonsymmetrical 2-aminobiphenyls with high selectivities. A heterogeneous palladium catalyst is used for the dehydrogenative cross-coupling of anilines with structurally diverse arenes. This reaction does not require stoichiometric oxidants and is an economical and environmentally friendly method.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b02527