Monoprotected l‐Amino Acid (l‐MPAA), Accelerated Bromination, Chlorination, and Iodination of C(sp2)−H Bonds by Iridium(III) Catalysis

Halogenated arenes are important structural motifs commonly found in biologically active molecules and used for a variety of transformations in organic synthesis. Herein, we report the mono‐protected l‐amino acid (l‐MPAA) accelerated iridium(III)‐catalyzed halogenation of (hetero)anilides at room te...

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Veröffentlicht in:Chemistry : a European journal 2017-05, Vol.23 (29), p.7031-7036
Hauptverfasser: Kathiravan, Subban, Nicholls, Ian A.
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Sprache:eng
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Zusammenfassung:Halogenated arenes are important structural motifs commonly found in biologically active molecules and used for a variety of transformations in organic synthesis. Herein, we report the mono‐protected l‐amino acid (l‐MPAA) accelerated iridium(III)‐catalyzed halogenation of (hetero)anilides at room temperature. This reaction constitutes the first example of an iridium(III)/l‐MPAA‐catalyzed general halogenation of (hetero)arenes through C(sp2)−H activation. Furthermore, we demonstrate the potential utility of our method through its use in the synthesis of a quinolone derivative. Fair trade: The versatile mono‐protected amino acid (l‐MPAA)‐promoted iridium(III)‐catalyzed halogenation of (hetero)anilides at room temperature is reported. The crucial role of l‐MPAA might be to generate an extremely reactive IrIII catalyst with a vacant site for amide coordination. A variety of anilides were efficiently converted into aryl halides and their synthetic utility in heterocyclic synthesis was demonstrated.
ISSN:0947-6539
1521-3765
1521-3765
DOI:10.1002/chem.201700280