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Visible-Light-Mediated Catalyst-Free [2+2] Cycloaddition Reaction for Dihydrocyclobuta[b]naphthalene-3,8-diones Synthesis under Mild Conditions

A facile and efficient visible-light-mediated method for directly converting 1,4-naphthoquinones into dihydrocyclo-buta[b]naphthalene-3,8-diones (DHCBNDOs) under mild and clean conditions without using any photocatalysts is reported. This approach exhibited favorable compatibility with functional gr...

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Autores principales: Tan, Hong-Bo, Zhou, Jia-Ying, Liu, Ying-Shan, Lei, Tong, Wang, Shi-Yu, Hu, Shuang-Shuang, Zhang, Xu, Xu, Zhi-Gang, Tang, Dian-Yong, Chen, Zhong-Zhu, Wang, Bo-Chu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10675681/
https://www.ncbi.nlm.nih.gov/pubmed/38005375
http://dx.doi.org/10.3390/molecules28227654
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author Tan, Hong-Bo
Zhou, Jia-Ying
Liu, Ying-Shan
Lei, Tong
Wang, Shi-Yu
Hu, Shuang-Shuang
Zhang, Xu
Xu, Zhi-Gang
Tang, Dian-Yong
Chen, Zhong-Zhu
Wang, Bo-Chu
author_facet Tan, Hong-Bo
Zhou, Jia-Ying
Liu, Ying-Shan
Lei, Tong
Wang, Shi-Yu
Hu, Shuang-Shuang
Zhang, Xu
Xu, Zhi-Gang
Tang, Dian-Yong
Chen, Zhong-Zhu
Wang, Bo-Chu
author_sort Tan, Hong-Bo
collection PubMed
description A facile and efficient visible-light-mediated method for directly converting 1,4-naphthoquinones into dihydrocyclo-buta[b]naphthalene-3,8-diones (DHCBNDOs) under mild and clean conditions without using any photocatalysts is reported. This approach exhibited favorable compatibility with functional groups and afforded a series of DHCBNDOs with excellent regioselectivity and high yields. Moreover, detailed mechanism studies were carried out both experimentally and theoretically. The readily accessible, low-cost and ecofriendly nature of the developed strategy will endow it with attractive applications in organic and medicinal chemistry.
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spelling pubmed-106756812023-11-18 Visible-Light-Mediated Catalyst-Free [2+2] Cycloaddition Reaction for Dihydrocyclobuta[b]naphthalene-3,8-diones Synthesis under Mild Conditions Tan, Hong-Bo Zhou, Jia-Ying Liu, Ying-Shan Lei, Tong Wang, Shi-Yu Hu, Shuang-Shuang Zhang, Xu Xu, Zhi-Gang Tang, Dian-Yong Chen, Zhong-Zhu Wang, Bo-Chu Molecules Article A facile and efficient visible-light-mediated method for directly converting 1,4-naphthoquinones into dihydrocyclo-buta[b]naphthalene-3,8-diones (DHCBNDOs) under mild and clean conditions without using any photocatalysts is reported. This approach exhibited favorable compatibility with functional groups and afforded a series of DHCBNDOs with excellent regioselectivity and high yields. Moreover, detailed mechanism studies were carried out both experimentally and theoretically. The readily accessible, low-cost and ecofriendly nature of the developed strategy will endow it with attractive applications in organic and medicinal chemistry. MDPI 2023-11-18 /pmc/articles/PMC10675681/ /pubmed/38005375 http://dx.doi.org/10.3390/molecules28227654 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Tan, Hong-Bo
Zhou, Jia-Ying
Liu, Ying-Shan
Lei, Tong
Wang, Shi-Yu
Hu, Shuang-Shuang
Zhang, Xu
Xu, Zhi-Gang
Tang, Dian-Yong
Chen, Zhong-Zhu
Wang, Bo-Chu
Visible-Light-Mediated Catalyst-Free [2+2] Cycloaddition Reaction for Dihydrocyclobuta[b]naphthalene-3,8-diones Synthesis under Mild Conditions
title Visible-Light-Mediated Catalyst-Free [2+2] Cycloaddition Reaction for Dihydrocyclobuta[b]naphthalene-3,8-diones Synthesis under Mild Conditions
title_full Visible-Light-Mediated Catalyst-Free [2+2] Cycloaddition Reaction for Dihydrocyclobuta[b]naphthalene-3,8-diones Synthesis under Mild Conditions
title_fullStr Visible-Light-Mediated Catalyst-Free [2+2] Cycloaddition Reaction for Dihydrocyclobuta[b]naphthalene-3,8-diones Synthesis under Mild Conditions
title_full_unstemmed Visible-Light-Mediated Catalyst-Free [2+2] Cycloaddition Reaction for Dihydrocyclobuta[b]naphthalene-3,8-diones Synthesis under Mild Conditions
title_short Visible-Light-Mediated Catalyst-Free [2+2] Cycloaddition Reaction for Dihydrocyclobuta[b]naphthalene-3,8-diones Synthesis under Mild Conditions
title_sort visible-light-mediated catalyst-free [2+2] cycloaddition reaction for dihydrocyclobuta[b]naphthalene-3,8-diones synthesis under mild conditions
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10675681/
https://www.ncbi.nlm.nih.gov/pubmed/38005375
http://dx.doi.org/10.3390/molecules28227654
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