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Programmable synthesis of multiply arylated cubanes through C–H metalation and arylation

Cubane (C(8)H(8)), a cubic alkane, has long attracted attention owing to its unique 3D structure. In order to utilize the cubane scaffold widely in science and technology, a powerful method for synthesizing diverse cubane derivatives is required. Herein, we report the synthesis of mono-, di-, tri-,...

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Detalles Bibliográficos
Autores principales: Okude, Ryo, Mori, Genki, Yagi, Akiko, Itami, Kenichiro
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8159448/
https://www.ncbi.nlm.nih.gov/pubmed/34094145
http://dx.doi.org/10.1039/d0sc01909g
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author Okude, Ryo
Mori, Genki
Yagi, Akiko
Itami, Kenichiro
author_facet Okude, Ryo
Mori, Genki
Yagi, Akiko
Itami, Kenichiro
author_sort Okude, Ryo
collection PubMed
description Cubane (C(8)H(8)), a cubic alkane, has long attracted attention owing to its unique 3D structure. In order to utilize the cubane scaffold widely in science and technology, a powerful method for synthesizing diverse cubane derivatives is required. Herein, we report the synthesis of mono-, di-, tri-, and tetra-arylated cubanes. Directed ortho-metalation with lithium base/alkyl zinc and subsequent palladium-catalyzed arylation enabled C–H metalation and arylation of cubane. This reaction allows the late-stage and regioselective installation of a wide range of aryl groups, realizing the first programmable synthesis of diverse multiply arylated cubanes.
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spelling pubmed-81594482021-06-04 Programmable synthesis of multiply arylated cubanes through C–H metalation and arylation Okude, Ryo Mori, Genki Yagi, Akiko Itami, Kenichiro Chem Sci Chemistry Cubane (C(8)H(8)), a cubic alkane, has long attracted attention owing to its unique 3D structure. In order to utilize the cubane scaffold widely in science and technology, a powerful method for synthesizing diverse cubane derivatives is required. Herein, we report the synthesis of mono-, di-, tri-, and tetra-arylated cubanes. Directed ortho-metalation with lithium base/alkyl zinc and subsequent palladium-catalyzed arylation enabled C–H metalation and arylation of cubane. This reaction allows the late-stage and regioselective installation of a wide range of aryl groups, realizing the first programmable synthesis of diverse multiply arylated cubanes. The Royal Society of Chemistry 2020-04-24 /pmc/articles/PMC8159448/ /pubmed/34094145 http://dx.doi.org/10.1039/d0sc01909g Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Okude, Ryo
Mori, Genki
Yagi, Akiko
Itami, Kenichiro
Programmable synthesis of multiply arylated cubanes through C–H metalation and arylation
title Programmable synthesis of multiply arylated cubanes through C–H metalation and arylation
title_full Programmable synthesis of multiply arylated cubanes through C–H metalation and arylation
title_fullStr Programmable synthesis of multiply arylated cubanes through C–H metalation and arylation
title_full_unstemmed Programmable synthesis of multiply arylated cubanes through C–H metalation and arylation
title_short Programmable synthesis of multiply arylated cubanes through C–H metalation and arylation
title_sort programmable synthesis of multiply arylated cubanes through c–h metalation and arylation
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8159448/
https://www.ncbi.nlm.nih.gov/pubmed/34094145
http://dx.doi.org/10.1039/d0sc01909g
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