Regio- and stereoselective access to highly substituted vinylphosphine oxides via metal-free electrophilic phosphonoiodination of alkynes

Bingbing Dong, Fengqian Zhao, Wen-Xin Lv, Ying-Guo Liu, Donghui Wei (), Junliang Wu () and Yonggui Robin Chi ()
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Bingbing Dong: Zhengzhou University
Fengqian Zhao: Zhengzhou University
Wen-Xin Lv: Guizhou University
Ying-Guo Liu: Zhengzhou University
Donghui Wei: Zhengzhou University
Junliang Wu: Zhengzhou University
Yonggui Robin Chi: Guizhou University

Nature Communications, 2024, vol. 15, issue 1, 1-9

Abstract: Abstract In general, the P-centered ring-opening of quaternary phosphirenium salts (QPrS) predominantly leads to hydrophosphorylated products, while the C-centered ring-opening is primarily confined to intramolecular nucleophilic reactions, resulting in the formation of phosphorus-containing cyclization products instead of difunctionalized products generated through intermolecular nucleophilic processes. Here, through the promotion of ring-opening of three-member rings by iodine anions and the quenching of electronegative carbon atoms by iodine cations, we successfully synthesize β-functionalized vinylphosphine oxides by the P-addition of QPrS intermediates generated in situ. Multiple β-iodo-substituted vinylphosphine oxides can be obtained with exceptional regio- and stereo-selectivity by reacting secondary phosphine oxides with unactivated alkynes. In addition, a variety of β-functionalized vinylphosphine oxides converted from C-I bonds, especially the rapid construction of benzo[b]phospholes oxides, demonstrates the significance of this strategy.

Date: 2024
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DOI: 10.1038/s41467-024-49640-z

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