Reactivity of Vinyl Epoxides/Oxetanes/Cyclopropanes toward Arynes: Access to Functionalized Phenanthrenes

[Image: see text] The reactivity of vinyl epoxides/oxetanes/cyclopropanes toward arynes has been demonstrated under mild conditions to give the corresponding phenanthrenes in moderate to good yields. This transition-metal-free cascade process involves a series of Diels–Alder reaction, ring-opening a...

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Autores principales: Liu, Jiupeng, Tang, Shuo, Zhao, Mengyao, Huai, Jianing, Yu, Jingya, Zhao, Jingjing, Li, Pan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8717566/
https://www.ncbi.nlm.nih.gov/pubmed/34984314
http://dx.doi.org/10.1021/acsomega.1c06166
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author Liu, Jiupeng
Tang, Shuo
Zhao, Mengyao
Huai, Jianing
Yu, Jingya
Zhao, Jingjing
Li, Pan
author_facet Liu, Jiupeng
Tang, Shuo
Zhao, Mengyao
Huai, Jianing
Yu, Jingya
Zhao, Jingjing
Li, Pan
author_sort Liu, Jiupeng
collection PubMed
description [Image: see text] The reactivity of vinyl epoxides/oxetanes/cyclopropanes toward arynes has been demonstrated under mild conditions to give the corresponding phenanthrenes in moderate to good yields. This transition-metal-free cascade process involves a series of Diels–Alder reaction, ring-opening aromatization, and ene reaction. Various functionalized phenanthrenes could be synthesized utilizing the versatile hydroxy group. Interestingly, vinyl epoxides/oxiranes experience preferentially the Diels–Alder reaction toward arynes over nucleophilic attack of epoxides/oxiranes.
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spelling pubmed-87175662022-01-03 Reactivity of Vinyl Epoxides/Oxetanes/Cyclopropanes toward Arynes: Access to Functionalized Phenanthrenes Liu, Jiupeng Tang, Shuo Zhao, Mengyao Huai, Jianing Yu, Jingya Zhao, Jingjing Li, Pan ACS Omega [Image: see text] The reactivity of vinyl epoxides/oxetanes/cyclopropanes toward arynes has been demonstrated under mild conditions to give the corresponding phenanthrenes in moderate to good yields. This transition-metal-free cascade process involves a series of Diels–Alder reaction, ring-opening aromatization, and ene reaction. Various functionalized phenanthrenes could be synthesized utilizing the versatile hydroxy group. Interestingly, vinyl epoxides/oxiranes experience preferentially the Diels–Alder reaction toward arynes over nucleophilic attack of epoxides/oxiranes. American Chemical Society 2021-12-15 /pmc/articles/PMC8717566/ /pubmed/34984314 http://dx.doi.org/10.1021/acsomega.1c06166 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Liu, Jiupeng
Tang, Shuo
Zhao, Mengyao
Huai, Jianing
Yu, Jingya
Zhao, Jingjing
Li, Pan
Reactivity of Vinyl Epoxides/Oxetanes/Cyclopropanes toward Arynes: Access to Functionalized Phenanthrenes
title Reactivity of Vinyl Epoxides/Oxetanes/Cyclopropanes toward Arynes: Access to Functionalized Phenanthrenes
title_full Reactivity of Vinyl Epoxides/Oxetanes/Cyclopropanes toward Arynes: Access to Functionalized Phenanthrenes
title_fullStr Reactivity of Vinyl Epoxides/Oxetanes/Cyclopropanes toward Arynes: Access to Functionalized Phenanthrenes
title_full_unstemmed Reactivity of Vinyl Epoxides/Oxetanes/Cyclopropanes toward Arynes: Access to Functionalized Phenanthrenes
title_short Reactivity of Vinyl Epoxides/Oxetanes/Cyclopropanes toward Arynes: Access to Functionalized Phenanthrenes
title_sort reactivity of vinyl epoxides/oxetanes/cyclopropanes toward arynes: access to functionalized phenanthrenes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8717566/
https://www.ncbi.nlm.nih.gov/pubmed/34984314
http://dx.doi.org/10.1021/acsomega.1c06166
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