期刊
GREEN CHEMISTRY
卷 24, 期 17, 页码 6481-+出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2gc01691e
关键词
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资金
- National Research Foundation of Korea [NRF-2020R1A2C2009636, NRF-2021R1A5A6002803, NRF-2019R1A2C2003969, NRF-2019R1A4A1029052]
A sustainable method has been developed to synthesize highly functionalized CF3-hydroquinone derivatives, which exhibit potent biological activity. The approach involves photoirradiation of a mixture containing readily available benzoquinones and CF3SO2Na, resulting in the generation of CF3-hydroquinones through photoinduced charge-transfer reactions. This method is practical, atom-economical, and enables site-selective three-component trifluoromethylation in the presence of vinyl arenes.
A distinctive sustainable approach has been developed to afford highly functionalized CF3-hydroquinone derivatives as potent biologically active molecules. The synthetic protocol involves the photoirradiation of a mixture of easily accessible benzoquinones and CF3SO2Na. This process generates a quinhydrone charge-transfer complex of benzoquinone and its in situ generated hydroquinone in the presence of a small amount of hydrogen donors, more preferably water. The subsequent formation of a transient ternary complex involving CF3SO2Na elicits photoinduced charge-transfer (CT), thereby producing CF3-hydroquinones. The present method is highly practical and atom-economical whilst avoiding the use of any sacrificial electron donors. Furthermore, the unique ternary complex intermediate permits site-selective three-component trifluoromethylation in the presence of vinyl arenes.
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