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

COLLEGE OF BIOTECHNOLOGY AND PHARMACEUTICAL ENGINEERING

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Journal	Organic Letters
DOIs	https://doi.org/10.1021/acs.orglett.5c02001
State	Accepted/In press - 2025

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10.1021/acs.orglett.5c02001

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

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.",

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

note = "Publisher Copyright: {\textcopyright} 2025 American Chemical Society.",

year = "2025",

doi = "10.1021/acs.orglett.5c02001",

language = "英语",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Silver-Mediated Dual Oxidation of 1,3-Dicarbonyls for Migration-Annulation

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.

UR - http://www.scopus.com/inward/record.url?scp=105009070769&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.5c02001

DO - 10.1021/acs.orglett.5c02001

M3 - 文章

AN - SCOPUS:105009070769

SN - 1523-7060

JO - Organic Letters

JF - Organic Letters

ER -

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

Abstract

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