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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...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2017
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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. |
format | Online Article Text |
id | pubmed-6645568 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
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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