Brønsted Base-Catalyzed Phosphorylation of Alkynes via Vinylidene -Quinone Methides.

Org Lett

School of Chemistry and Chemical Engineering, Guangxi Colleges and Universities Key Laboratory of Applied Chemistry Technology and Resource Development, Guangxi University, Nanning 530004, China.

Published: September 2025


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Article Abstract

Vinylphosphonates serve as crucial components in synthetic chemistry, medicinal chemistry, and materials science. However, traditional synthetic methods for these compounds typically require the use of noble metal catalysts and hazardous reagents. Herein, we report a metal-free strategy for the divergent synthesis of vinylphosphonates through the P nucleophilic addition of vinylidene -quinone methides (-VQMs). This method provides a variety of 1,2-diaryl vinylphosphates in good yields (up to 85% yield), which represents a unique example of -VQMs for C-P bond formation. The protocol features mild reaction conditions, a green solvent, broad functional group compatibility, and environmental friendliness.

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http://dx.doi.org/10.1021/acs.orglett.5c03542DOI Listing

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