Phosphinothio(seleno)ation of alkynes/olefins and application on the late-stage functionalization of natural products

Non-metallic catalysis has been known as a remarkable development strategy for hydrofunctionalization of unsaturated hydrocarbons. Herein, we report a unique chemically active method of BF 3 ·OEt 2 promoted multi-component, highly regioselective, and chemoselective hydrothio(seleo)phosphonylation of...

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Bibliographic Details
Published in:Communications chemistry 2024-12, Vol.7 (1), p.290-13, Article 290
Main Authors: Shao, Chang-Wei, Wan, Pei-Feng, Xu, Quan, Yang, Ze-Nan, Geng, Mei-Yu, Zhang, Yu, Zhang, Xing-Hua, Li, Xu-Wen
Format: Article
Language:English
Subjects:
631/154/309
639/638/403/933
639/638/403/977
Alkenes
Alkynes
Catalysis
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Hydrocarbons
Lewis acid
Natural products
NMR
Nuclear magnetic resonance
Parkinson's disease
Reaction mechanisms
Regioselectivity
Transition metals
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Summary:Non-metallic catalysis has been known as a remarkable development strategy for hydrofunctionalization of unsaturated hydrocarbons. Herein, we report a unique chemically active method of BF 3 ·OEt 2 promoted multi-component, highly regioselective, and chemoselective hydrothio(seleo)phosphonylation of unsaturated hydrocarbons, which exhibits high yield and good substrate universality. The reaction mechanism was further elucidated to be Markovnikov addition by controlling experiments, 31 P and 19 F NMR spectra tracking experiments, X-ray diffraction analysis, and DFT calculations. Furthermore, the gram-scale attempt and the application of the reaction on the derivatization of natural products have been successfully conducted, leading to the discovery of 3as with potential anti-Parkinson's disease (PD) activities at 1 μM. This streamlined and efficient methodology has established a new platform for non-metallic Lewis acids-promoted hydrofunctionalization of unsaturated hydrocarbons and its application on new drug research. Transition metal catalysts are typically used for the hydrofunctionalization of unsaturated hydrocarbons, however, such reactions are time-consuming and may be challenging. Herein, the authors report the non-metallic BF 3 ·OEt 2 -promoted multi-component, highly regioselective, and chemoselective hydrothio(seleo)phosphonylation of unsaturated hydrocarbons, which exhibits high yields and good substrate universality
ISSN:2399-3669
2399-3669
DOI:10.1038/s42004-024-01326-9