Helicene synthesis by Brønsted acid-catalyzed cycloaromatization in HFIP [(CF(3))(2)CHOH]

A facile synthesis of carbo- and heterohelicenes was achieved via tandem cycloaromatization of bisacetal precursors, which were readily prepared through C–C bond formation by Suzuki–Miyaura coupling. This cyclization was efficiently realized by a catalytic amount of trifluoromethanesulfonic acid (Tf...

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Detalles Bibliográficos
Autores principales: Fujita, Takeshi, Shoji, Noriaki, Yoshikawa, Nao, Ichikawa, Junji
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2021
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7884880/
https://www.ncbi.nlm.nih.gov/pubmed/33633807
http://dx.doi.org/10.3762/bjoc.17.35
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author Fujita, Takeshi
Shoji, Noriaki
Yoshikawa, Nao
Ichikawa, Junji
author_facet Fujita, Takeshi
Shoji, Noriaki
Yoshikawa, Nao
Ichikawa, Junji
author_sort Fujita, Takeshi
collection PubMed
description A facile synthesis of carbo- and heterohelicenes was achieved via tandem cycloaromatization of bisacetal precursors, which were readily prepared through C–C bond formation by Suzuki–Miyaura coupling. This cyclization was efficiently realized by a catalytic amount of trifluoromethanesulfonic acid (TfOH) in a cation-stabilizing solvent, 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP), which readily allowed gram-scale syntheses of higher-order helicenes, double helical helicenes, and heterohelicenes.
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spelling pubmed-78848802021-02-24 Helicene synthesis by Brønsted acid-catalyzed cycloaromatization in HFIP [(CF(3))(2)CHOH] Fujita, Takeshi Shoji, Noriaki Yoshikawa, Nao Ichikawa, Junji Beilstein J Org Chem Full Research Paper A facile synthesis of carbo- and heterohelicenes was achieved via tandem cycloaromatization of bisacetal precursors, which were readily prepared through C–C bond formation by Suzuki–Miyaura coupling. This cyclization was efficiently realized by a catalytic amount of trifluoromethanesulfonic acid (TfOH) in a cation-stabilizing solvent, 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP), which readily allowed gram-scale syntheses of higher-order helicenes, double helical helicenes, and heterohelicenes. Beilstein-Institut 2021-02-09 /pmc/articles/PMC7884880/ /pubmed/33633807 http://dx.doi.org/10.3762/bjoc.17.35 Text en Copyright © 2021, Fujita et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/terms/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the author(s) and source are credited and that individual graphics may be subject to special legal provisions. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms/terms)
spellingShingle Full Research Paper
Fujita, Takeshi
Shoji, Noriaki
Yoshikawa, Nao
Ichikawa, Junji
Helicene synthesis by Brønsted acid-catalyzed cycloaromatization in HFIP [(CF(3))(2)CHOH]
title Helicene synthesis by Brønsted acid-catalyzed cycloaromatization in HFIP [(CF(3))(2)CHOH]
title_full Helicene synthesis by Brønsted acid-catalyzed cycloaromatization in HFIP [(CF(3))(2)CHOH]
title_fullStr Helicene synthesis by Brønsted acid-catalyzed cycloaromatization in HFIP [(CF(3))(2)CHOH]
title_full_unstemmed Helicene synthesis by Brønsted acid-catalyzed cycloaromatization in HFIP [(CF(3))(2)CHOH]
title_short Helicene synthesis by Brønsted acid-catalyzed cycloaromatization in HFIP [(CF(3))(2)CHOH]
title_sort helicene synthesis by brønsted acid-catalyzed cycloaromatization in hfip [(cf(3))(2)choh]
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7884880/
https://www.ncbi.nlm.nih.gov/pubmed/33633807
http://dx.doi.org/10.3762/bjoc.17.35
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