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

ABSTRACT: 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.

SUBMITTER: Liu J

PROVIDER: S-EPMC8717566 | biostudies-literature | 2021 Dec

REPOSITORIES: biostudies-literature

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

Liu Jiupeng J Tang Shuo S Zhao Mengyao M Huai Jianing J Yu Jingya J Zhao Jingjing J Li Pan P

ACS omega 20211215 51

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 ...[more]

PMID: 34984314

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