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

Autor: Li J; Department Chemie , Ludwig-Maximilians-Universität München , Butenandtstraße 5-13, Haus F , 81377 Munich , Germany.; School of Pharmaceutical Science , Jiangnan University , Lihu Road 1800 , 214122 Wuxi , Jiangsu , China., Tan E; Department Chemie , Ludwig-Maximilians-Universität München , Butenandtstraße 5-13, Haus F , 81377 Munich , Germany., Keller N; Department Chemie , Ludwig-Maximilians-Universität München , Butenandtstraße 5-13, Haus F , 81377 Munich , Germany., Chen YH; Department Chemie , Ludwig-Maximilians-Universität München , Butenandtstraße 5-13, Haus F , 81377 Munich , Germany., Zehetmaier PM; Department Chemie , Ludwig-Maximilians-Universität München , Butenandtstraße 5-13, Haus F , 81377 Munich , Germany., Jakowetz AC; Department Chemie , Ludwig-Maximilians-Universität München , Butenandtstraße 5-13, Haus F , 81377 Munich , Germany., Bein T; Department Chemie , Ludwig-Maximilians-Universität München , Butenandtstraße 5-13, Haus F , 81377 Munich , Germany., Knochel P; Department Chemie , Ludwig-Maximilians-Universität München , Butenandtstraße 5-13, Haus F , 81377 Munich , Germany.
Jazyk: angličtina
Zdroj: Journal of the American Chemical Society [J Am Chem Soc] 2019 Jan 09; Vol. 141 (1), pp. 98-103. Date of Electronic Publication: 2018 Dec 21.
DOI: 10.1021/jacs.8b11466
Abstrakt: 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.
Databáze: MEDLINE
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