Sustainable photoredox chemistry of a transient ternary complex: an unconventional approach toward trifluoromethylated hydroquinones
- Authors
- Lee, Da Seul; Soni, Vineet Kumar; Heo, Seunga; Hwang, Ho Seong; You, Youngmin; Cho, Eun Jin
- Issue Date
- Aug-2022
- Publisher
- ROYAL SOC CHEMISTRY
- Citation
- GREEN CHEMISTRY, v.24, no.17, pp 6481 - 6486
- Pages
- 6
- Journal Title
- GREEN CHEMISTRY
- Volume
- 24
- Number
- 17
- Start Page
- 6481
- End Page
- 6486
- URI
- https://scholarworks.bwise.kr/cau/handle/2019.sw.cau/58335
- DOI
- 10.1039/d2gc01691e
- ISSN
- 1463-9262
1463-9270
- Abstract
- 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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Collections - College of Natural Sciences > Department of Chemistry > 1. Journal Articles
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