研究目的
Developing a green and sustainable radical reaction for the hydrogenation and arylsulfonylation of alkenes using a photoinduced strategy without external photocatalysts, oxidants, or reductants.
研究成果
The developed method provides an efficient, photocatalyst-free, oxidant-free, and reductant-free approach for the hydrogenation of C6-(vinyl sulfone)phenanthridines and arylsulfonylation of N-arylacrylamides in one pot, yielding products in high yields with broad substrate scope. The reaction is driven by photochemical activity of hydrogen bond donor-acceptor complexes, offering a green and sustainable alternative for radical transformations. Future work will explore applications of these complexes in organic synthesis.
研究不足
The reaction requires specific UV light (380±5 nm) and does not proceed under visible light (e.g., blue or green LED), air atmosphere, or in the dark. It is sensitive to steric hindrance, with ortho-substituted substrates showing reduced reactivity or failure. The scope is limited to certain alkene and sulfinic acid types, and the mechanism, while plausible, is not fully elucidated.
1：Experimental Design and Method Selection:
The study involves a one-pot reaction under UV light irradiation (380±5 nm) in acetonitrile solvent under N2 atmosphere, utilizing hydrogen bond donor-acceptor complexes formed from arylsulfinic acids and alkenes (C6-(vinyl sulfone)phenanthridines or N-arylacrylamides) to generate hydrogen and sulfonyl radicals.
2：Sample Selection and Data Sources:
Substrates include various (Z)-C6-(vinyl sulfone)phenanthridines, N-arylacrylamides, and arylsulfinic acids, selected based on electronic and steric properties.
3：List of Experimental Equipment and Materials:
Equipment includes UV LED light source (380±5 nm, 3 W), NMR spectrometer (Bruker Avance, 400 MHz or 100 MHz), mass spectrometer (Agilent Technologies 6540 UHD Accurate-Mass Q-TOF LC/MS), and standard laboratory glassware. Materials include acetonitrile, arylsulfinic acids, alkenes, and silica gel for chromatography.
4：Experimental Procedures and Operational Workflow:
Substrates and arylsulfinic acid are mixed in acetonitrile in an air-tight reaction tube, evacuated and back-filled with N2, stirred under UV irradiation at room temperature for 24 hours, then purified by flash chromatography.
5：Data Analysis Methods:
Products are characterized by 1H NMR, 13C NMR, and HRMS; reaction yields are determined by isolated yields; mechanistic studies include UV/vis spectroscopy, NMR spectroscopy, computational modeling (M06-2X/6-31G(d,p) with IEFPCM), and radical-trapping experiments with TEMPO.
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