Photochemical synthesis of 3-hydroxyphenanthro[9,10-c]furan-1(3H)-ones from α-keto acids and alkynes

Beibei Zhao; Zhen Zhang; Yu Ge; Pinhua Li; Tao Miao; Lei Wang

doi:10.1039/D0QO01487G

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Photochemical synthesis of 3-hydroxyphenanthro[9,10-c]furan-1(3H)-ones from α-keto acids and alkynes†

Beibei Zhao,^a Zhen Zhang,^a Yu Ge,^a Pinhua Li,

^a Tao Miao*^a and Lei Wang

*^abc

Author affiliations

* Corresponding authors

^a Department of Chemistry; Key Laboratory of Green and Precise Synthetic Chemistry, Ministry of Education, Huaibei Normal University, Huaibei, Anhui 235000, P. R. China
E-mail: taomiao@chnu.edu.cn

^b Advanced Research Institute and Department of Chemistry, Taizhou University, Taizhou, Zhejiang 318000, P. R. China
E-mail: leiwang88@hotmail.com

^c State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P R China

Abstract

A novel and efficient method for the synthesis of 3-hydroxyphenanthro[9,10-c]furan-1(3H)-ones has been achieved from readily available α-keto acids and alkynes through photo-initiated transformation, providing a range of structurally diverse products in good to excellent yields under mild conditions. Mechanistic studies reveal that this reaction undergoes photo-induced radical addition/cyclization and hydrogen evolution cascade processes.

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DOI: https://doi.org/10.1039/D0QO01487G
Article type: Research Article
Submitted: 29 Nov 2020
Accepted: 31 Dec 2020
First published: 04 Jan 2021

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Org. Chem. Front., 2021,8, 975-982

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Photochemical synthesis of 3-hydroxyphenanthro[9,10-c]furan-1(3H)-ones from α-keto acids and alkynes

B. Zhao, Z. Zhang, Y. Ge, P. Li, T. Miao and L. Wang, Org. Chem. Front., 2021, 8, 975 DOI: 10.1039/D0QO01487G

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Organic Chemistry Frontiers

Photochemical synthesis of 3-hydroxyphenanthro[9,10-c]furan-1(3H)-ones from α-keto acids and alkynes†

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Photochemical synthesis of 3-hydroxyphenanthro[9,10-c]furan-1(3H)-ones from α-keto acids and alkynes

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