Cobalt-Catalyzed Electrophilic Aminations with Anthranils: An Expedient Route to Condensed Quinolines | Zendy

Jie Li | Zendy; Eric Tan | Zendy; Niklas Keller | Zendy; YiHung Chen | Zendy; Peter M. Zehetmaier | Zendy; Andreas C. Jakowetz | Zendy; Thomas Bein | Zendy; Paul Knochel | Zendy

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Cobalt-Catalyzed Electrophilic Aminations with Anthranils: An Expedient Route to Condensed Quinolines

Author(s) -

Jie Li,

Eric Tan,

Niklas Keller,

YiHung Chen,

Peter M. Zehetmaier,

Andreas C. Jakowetz,

Thomas Bein,

Paul Knochel

Publication year - 2018

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.8b11466

Subject(s) - chemistry , electrophile , catalysis , photoluminescence , iodide , cobalt , exciton , combinatorial chemistry , band gap , diode , photochemistry , inorganic chemistry , organic chemistry , optoelectronics , materials science , physics , quantum mechanics

The reaction of various organozinc pivalates with anthranils provides anilines derivatives, which cyclize under acidic conditions providing condensed quinolines. Using alkenylzinc pivalates, electron-rich arylzinc pivalates or heterocyclic zinc pivalates produces directly the condensed quinolines of which several structures belong to new heterocyclic scaffolds. These N-heterocycles are of particular interest for organic light emitting diodes with their high photoluminescence quantum yields and long exciton lifetimes as well as for hole-transporting materials in methylammonium lead iodide perovskites solar cells due to an optimal band alignment for holes and a large bandgap.

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