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Photocatalytic synthesis of tetra-substituted furans promoted by carbon dioxide.

ABSTRACT: We report a simple protocol for the transition metal-free, visible-light-driven conversion of 1,3-diketones to tetra-substituted furan skeleton compounds in carbon dioxide (CO₂) atmosphere under mild conditions. It was found that CO₂ could be incorporated at the diketone enolic OH position, which was key to enabling the cleavage of a C-O bond during the rearrangement of a cyclopropane intermediate. This method allows for the same-pot construction of two isomers of the high-value tetra-substituted furan scaffold. The synthetic scope and preliminary mechanistic investigations are presented.

SUBMITTER: Tian YM

PROVIDER: S-EPMC8694347 | biostudies-literature | 2021 Dec

REPOSITORIES: biostudies-literature

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Photocatalytic synthesis of tetra-substituted furans promoted by carbon dioxide.

Tian Ya-Ming YM Wang Huaiju H Ritu König Burkhard B

Chemical science 20211206 1

We report a simple protocol for the transition metal-free, visible-light-driven conversion of 1,3-diketones to tetra-substituted furan skeleton compounds in carbon dioxide (CO2) atmosphere under mild conditions. It was found that CO2 could be incorporated at the diketone enolic OH position, which was key to enabling the cleavage of a C-O bond during the rearrangement of a cyclopropane intermediate. This method allows for the same-pot construction of two isomers of the high- ...[more]

PMID: 35059173

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