Copper-Catalyzed Phosphorylation of 2,3-Allenoic Acids and Phosphine Oxide: Access to Phosphorylated Butenolides

We investigated a novel Cu-catalyzed annulation of 2,3-allenoic acids with diphenylphosphine oxide, leading to the formation of 4-phosphate butenolides in up to 88% yield. The formation of the C–P bond provides new avenues for the functionalization of different furan-2­(5H)-ones, with favorable feat...

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Bibliographic Details
Published in:Journal of organic chemistry 2021-07, Vol.86 (14), p.9699-9710
Main Authors: Zhong, Tianshuo, Zheng, Xiangyun, Yin, Chuanliu, Shen, Qitao, Yu, Chuanming
Format: Article
Language:English
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Summary:We investigated a novel Cu-catalyzed annulation of 2,3-allenoic acids with diphenylphosphine oxide, leading to the formation of 4-phosphate butenolides in up to 88% yield. The formation of the C–P bond provides new avenues for the functionalization of different furan-2­(5H)-ones, with favorable features such as suitable functional group tolerance and mild synthesis conditions.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c00998