1,1-Oxycarbonation of Terminal Alkynes via Sequential Borylation, 1,2-Migration, and Oxidation with Oxone

Alkynes are readily available and multifunctional synthetic intermediates, but their 1,1-oxofunctionalization remains challenging. Herein, we report a 1,1-oxycarbonation of terminal alkynes to construct ketones through sequential borylation, 1,2-carbon migration, and oxidation with Oxone as the prot...

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Bibliographic Details
Published in:Organic letters 2024-04, Vol.26 (15), p.3109-3113
Main Authors: Zhang, Guan, Feng, Bofan, Wang, Yutong, Chen, Jinglong, Ma, Xingxing, Song, Qiuling
Format: Article
Language:English
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Summary:Alkynes are readily available and multifunctional synthetic intermediates, but their 1,1-oxofunctionalization remains challenging. Herein, we report a 1,1-oxycarbonation of terminal alkynes to construct ketones through sequential borylation, 1,2-carbon migration, and oxidation with Oxone as the proton source and oxidant. The synthetic potential of this transformation is showcased by the broad functional groups, scale-up synthesis, and diverse product transformations.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.4c00738