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

[Image: see text] 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 conde...

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Autores principales: Li, Jie, Tan, Eric, Keller, Niklas, Chen, Yi-Hung, Zehetmaier, Peter M., Jakowetz, Andreas C., Bein, Thomas, Knochel, Paul
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6400427/
https://www.ncbi.nlm.nih.gov/pubmed/30558415
http://dx.doi.org/10.1021/jacs.8b11466
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author Li, Jie
Tan, Eric
Keller, Niklas
Chen, Yi-Hung
Zehetmaier, Peter M.
Jakowetz, Andreas C.
Bein, Thomas
Knochel, Paul
author_facet Li, Jie
Tan, Eric
Keller, Niklas
Chen, Yi-Hung
Zehetmaier, Peter M.
Jakowetz, Andreas C.
Bein, Thomas
Knochel, Paul
author_sort Li, Jie
collection PubMed
description [Image: see text] 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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spelling pubmed-64004272019-03-06 Cobalt-Catalyzed Electrophilic Aminations with Anthranils: An Expedient Route to Condensed Quinolines Li, Jie Tan, Eric Keller, Niklas Chen, Yi-Hung Zehetmaier, Peter M. Jakowetz, Andreas C. Bein, Thomas Knochel, Paul J Am Chem Soc [Image: see text] 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. American Chemical Society 2018-12-18 2019-01-09 /pmc/articles/PMC6400427/ /pubmed/30558415 http://dx.doi.org/10.1021/jacs.8b11466 Text en Copyright © 2018 American Chemical Society This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License (http://pubs.acs.org/page/policy/authorchoice_ccbyncnd_termsofuse.html) , which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes.
spellingShingle Li, Jie
Tan, Eric
Keller, Niklas
Chen, Yi-Hung
Zehetmaier, Peter M.
Jakowetz, Andreas C.
Bein, Thomas
Knochel, Paul
Cobalt-Catalyzed Electrophilic Aminations with Anthranils: An Expedient Route to Condensed Quinolines
title Cobalt-Catalyzed Electrophilic Aminations with Anthranils: An Expedient Route to Condensed Quinolines
title_full Cobalt-Catalyzed Electrophilic Aminations with Anthranils: An Expedient Route to Condensed Quinolines
title_fullStr Cobalt-Catalyzed Electrophilic Aminations with Anthranils: An Expedient Route to Condensed Quinolines
title_full_unstemmed Cobalt-Catalyzed Electrophilic Aminations with Anthranils: An Expedient Route to Condensed Quinolines
title_short Cobalt-Catalyzed Electrophilic Aminations with Anthranils: An Expedient Route to Condensed Quinolines
title_sort cobalt-catalyzed electrophilic aminations with anthranils: an expedient route to condensed quinolines
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6400427/
https://www.ncbi.nlm.nih.gov/pubmed/30558415
http://dx.doi.org/10.1021/jacs.8b11466
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