Rapid Access to Hydroxyfluoranthenes via a Domino Suzuki–Miyaura/Intramolecular Diels–Alder/Ring-Opening Reactions Sequence

[Image: see text] In this work, we developed an efficient method for the rapid construction of fluoranthene skeleton to access a variety of substituted hydroxyfluoranthenes. The 1-iodo-8-alkynylnaphthalene derivatives, which serve as substrates for the key fluoranthene-forming step, were prepared vi...

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Autores principales: Ahmadli, Dilgam, Sahin, Yesim, Calikyilmaz, Eylul, Şahin, Onur, Türkmen, Yunus E.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9087347/
https://www.ncbi.nlm.nih.gov/pubmed/35389218
http://dx.doi.org/10.1021/acs.joc.1c03080
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author Ahmadli, Dilgam
Sahin, Yesim
Calikyilmaz, Eylul
Şahin, Onur
Türkmen, Yunus E.
author_facet Ahmadli, Dilgam
Sahin, Yesim
Calikyilmaz, Eylul
Şahin, Onur
Türkmen, Yunus E.
author_sort Ahmadli, Dilgam
collection PubMed
description [Image: see text] In this work, we developed an efficient method for the rapid construction of fluoranthene skeleton to access a variety of substituted hydroxyfluoranthenes. The 1-iodo-8-alkynylnaphthalene derivatives, which serve as substrates for the key fluoranthene-forming step, were prepared via selective monoalkynylative Sonogashira reactions of 1,8-diiodonaphthalene. The domino reaction sequence which involves a sequential Suzuki–Miyaura coupling, an intramolecular Diels–Alder reaction, and an aromatization-driven ring-opening isomerization has been shown to give substituted hydroxyfluoranthenes in up to 92% yield. This work demonstrates the utility of designing new domino reactions for rapid access to substituted polycyclic aromatic hydrocarbons (PAHs).
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spelling pubmed-90873472022-05-11 Rapid Access to Hydroxyfluoranthenes via a Domino Suzuki–Miyaura/Intramolecular Diels–Alder/Ring-Opening Reactions Sequence Ahmadli, Dilgam Sahin, Yesim Calikyilmaz, Eylul Şahin, Onur Türkmen, Yunus E. J Org Chem [Image: see text] In this work, we developed an efficient method for the rapid construction of fluoranthene skeleton to access a variety of substituted hydroxyfluoranthenes. The 1-iodo-8-alkynylnaphthalene derivatives, which serve as substrates for the key fluoranthene-forming step, were prepared via selective monoalkynylative Sonogashira reactions of 1,8-diiodonaphthalene. The domino reaction sequence which involves a sequential Suzuki–Miyaura coupling, an intramolecular Diels–Alder reaction, and an aromatization-driven ring-opening isomerization has been shown to give substituted hydroxyfluoranthenes in up to 92% yield. This work demonstrates the utility of designing new domino reactions for rapid access to substituted polycyclic aromatic hydrocarbons (PAHs). American Chemical Society 2022-04-07 2022-05-06 /pmc/articles/PMC9087347/ /pubmed/35389218 http://dx.doi.org/10.1021/acs.joc.1c03080 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Ahmadli, Dilgam
Sahin, Yesim
Calikyilmaz, Eylul
Şahin, Onur
Türkmen, Yunus E.
Rapid Access to Hydroxyfluoranthenes via a Domino Suzuki–Miyaura/Intramolecular Diels–Alder/Ring-Opening Reactions Sequence
title Rapid Access to Hydroxyfluoranthenes via a Domino Suzuki–Miyaura/Intramolecular Diels–Alder/Ring-Opening Reactions Sequence
title_full Rapid Access to Hydroxyfluoranthenes via a Domino Suzuki–Miyaura/Intramolecular Diels–Alder/Ring-Opening Reactions Sequence
title_fullStr Rapid Access to Hydroxyfluoranthenes via a Domino Suzuki–Miyaura/Intramolecular Diels–Alder/Ring-Opening Reactions Sequence
title_full_unstemmed Rapid Access to Hydroxyfluoranthenes via a Domino Suzuki–Miyaura/Intramolecular Diels–Alder/Ring-Opening Reactions Sequence
title_short Rapid Access to Hydroxyfluoranthenes via a Domino Suzuki–Miyaura/Intramolecular Diels–Alder/Ring-Opening Reactions Sequence
title_sort rapid access to hydroxyfluoranthenes via a domino suzuki–miyaura/intramolecular diels–alder/ring-opening reactions sequence
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9087347/
https://www.ncbi.nlm.nih.gov/pubmed/35389218
http://dx.doi.org/10.1021/acs.joc.1c03080
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