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Synthesis of Fluoranthene Derivatives via Tandem Suzuki–Miyaura and Intramolecular C–H Arylation Reactions under Both Homogeneous and Heterogeneous Catalytic Conditions

[Image: see text] A catalytic method for the synthesis of substituted fluoranthenes that operates via tandem Suzuki–Miyaura and intramolecular C–H arylation reactions is reported. The overall reaction sequence works effectively with homogeneous catalysis using Pd(dppf)Cl(2) as well as heterogeneous...

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Autores principales: Pal, Sujit, Metin, Önder, Türkmen, Yunus E.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2017
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6645568/
https://www.ncbi.nlm.nih.gov/pubmed/31457400
http://dx.doi.org/10.1021/acsomega.7b01566
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author Pal, Sujit
Metin, Önder
Türkmen, Yunus E.
author_facet Pal, Sujit
Metin, Önder
Türkmen, Yunus E.
author_sort Pal, Sujit
collection PubMed
description [Image: see text] A catalytic method for the synthesis of substituted fluoranthenes that operates via tandem Suzuki–Miyaura and intramolecular C–H arylation reactions is reported. The overall reaction sequence works effectively with homogeneous catalysis using Pd(dppf)Cl(2) as well as heterogeneous catalysis using reduced graphene oxide (rGO)-CuPd nanocatalysts with low catalyst loadings. High functional group tolerance is observed under both catalytic conditions where arylboronic acids and esters having electron-withdrawing and electron-donating substituents afforded fluoranthene products in good yields (up to 78%). Moreover, the rGO-CuPd nanocatalysts are demonstrated to be reusable by preserving almost 90% of their initial activity after the third cycle.
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spelling pubmed-66455682019-08-27 Synthesis of Fluoranthene Derivatives via Tandem Suzuki–Miyaura and Intramolecular C–H Arylation Reactions under Both Homogeneous and Heterogeneous Catalytic Conditions Pal, Sujit Metin, Önder Türkmen, Yunus E. ACS Omega [Image: see text] A catalytic method for the synthesis of substituted fluoranthenes that operates via tandem Suzuki–Miyaura and intramolecular C–H arylation reactions is reported. The overall reaction sequence works effectively with homogeneous catalysis using Pd(dppf)Cl(2) as well as heterogeneous catalysis using reduced graphene oxide (rGO)-CuPd nanocatalysts with low catalyst loadings. High functional group tolerance is observed under both catalytic conditions where arylboronic acids and esters having electron-withdrawing and electron-donating substituents afforded fluoranthene products in good yields (up to 78%). Moreover, the rGO-CuPd nanocatalysts are demonstrated to be reusable by preserving almost 90% of their initial activity after the third cycle. American Chemical Society 2017-12-07 /pmc/articles/PMC6645568/ /pubmed/31457400 http://dx.doi.org/10.1021/acsomega.7b01566 Text en Copyright © 2017 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Pal, Sujit
Metin, Önder
Türkmen, Yunus E.
Synthesis of Fluoranthene Derivatives via Tandem Suzuki–Miyaura and Intramolecular C–H Arylation Reactions under Both Homogeneous and Heterogeneous Catalytic Conditions
title Synthesis of Fluoranthene Derivatives via Tandem Suzuki–Miyaura and Intramolecular C–H Arylation Reactions under Both Homogeneous and Heterogeneous Catalytic Conditions
title_full Synthesis of Fluoranthene Derivatives via Tandem Suzuki–Miyaura and Intramolecular C–H Arylation Reactions under Both Homogeneous and Heterogeneous Catalytic Conditions
title_fullStr Synthesis of Fluoranthene Derivatives via Tandem Suzuki–Miyaura and Intramolecular C–H Arylation Reactions under Both Homogeneous and Heterogeneous Catalytic Conditions
title_full_unstemmed Synthesis of Fluoranthene Derivatives via Tandem Suzuki–Miyaura and Intramolecular C–H Arylation Reactions under Both Homogeneous and Heterogeneous Catalytic Conditions
title_short Synthesis of Fluoranthene Derivatives via Tandem Suzuki–Miyaura and Intramolecular C–H Arylation Reactions under Both Homogeneous and Heterogeneous Catalytic Conditions
title_sort synthesis of fluoranthene derivatives via tandem suzuki–miyaura and intramolecular c–h arylation reactions under both homogeneous and heterogeneous catalytic conditions
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6645568/
https://www.ncbi.nlm.nih.gov/pubmed/31457400
http://dx.doi.org/10.1021/acsomega.7b01566
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