Silver-Mediated Dual Oxidation of 1,3-Dicarbonyls for Migration-Annulation

Ziren Mao; Hongyan Xu; Jingming Zhang; Xiangxing Huang; Chengkou Liu; Hong Qin; Yuguang Li; Zhao Yang; Zheng Fang

doi:10.1021/acs.orglett.5c02001

Silver-Mediated Dual Oxidation of 1,3-Dicarbonyls for Migration-Annulation

Ziren Mao, Hongyan Xu, Jingming Zhang, Xiangxing Huang, Chengkou Liu, Hong Qin, Yuguang Li, Zhao Yang, Zheng Fang

生物与制药工程学院

科研成果: 期刊稿件 › 文章 › 同行评审

摘要

A new type of radical cascade reaction has been reported, by which free radicals were generated twice successively through the implementation of dual oxidation on a 1,3-dicarbonyl compound in a single operation, thereby realizing a conceptually novel alkynyl migration-annulation mode. The reaction involved addition, 1,2-alkynyl migration, and 4-exo-dig/6-endo-trig bicyclization under mild reaction conditions, offering an efficient route to tetrahydrocyclobuta[b]naphthalene in good yields. Control experiments revealed migration products as key intermediates and elucidated the step sequence in these transformations.

源语言	英语
期刊	Organic Letters
DOI	https://doi.org/10.1021/acs.orglett.5c02001
出版状态	已接受/待刊 - 2025

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10.1021/acs.orglett.5c02001

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引用此

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abstract = "A new type of radical cascade reaction has been reported, by which free radicals were generated twice successively through the implementation of dual oxidation on a 1,3-dicarbonyl compound in a single operation, thereby realizing a conceptually novel alkynyl migration-annulation mode. The reaction involved addition, 1,2-alkynyl migration, and 4-exo-dig/6-endo-trig bicyclization under mild reaction conditions, offering an efficient route to tetrahydrocyclobuta[b]naphthalene in good yields. Control experiments revealed migration products as key intermediates and elucidated the step sequence in these transformations.",

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AU - Mao, Ziren

AU - Xu, Hongyan

AU - Zhang, Jingming

AU - Huang, Xiangxing

AU - Liu, Chengkou

AU - Qin, Hong

AU - Li, Yuguang

AU - Yang, Zhao

AU - Fang, Zheng

PY - 2025

Y1 - 2025

N2 - A new type of radical cascade reaction has been reported, by which free radicals were generated twice successively through the implementation of dual oxidation on a 1,3-dicarbonyl compound in a single operation, thereby realizing a conceptually novel alkynyl migration-annulation mode. The reaction involved addition, 1,2-alkynyl migration, and 4-exo-dig/6-endo-trig bicyclization under mild reaction conditions, offering an efficient route to tetrahydrocyclobuta[b]naphthalene in good yields. Control experiments revealed migration products as key intermediates and elucidated the step sequence in these transformations.

AB - A new type of radical cascade reaction has been reported, by which free radicals were generated twice successively through the implementation of dual oxidation on a 1,3-dicarbonyl compound in a single operation, thereby realizing a conceptually novel alkynyl migration-annulation mode. The reaction involved addition, 1,2-alkynyl migration, and 4-exo-dig/6-endo-trig bicyclization under mild reaction conditions, offering an efficient route to tetrahydrocyclobuta[b]naphthalene in good yields. Control experiments revealed migration products as key intermediates and elucidated the step sequence in these transformations.

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DO - 10.1021/acs.orglett.5c02001

M3 - 文章

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SN - 1523-7060

JO - Organic Letters

JF - Organic Letters

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