Journal
ORGANIC LETTERS
Volume 24, Issue 32, Pages 5918-5923Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c02150
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Funding
- National Natural Science Foundation of China [21907052]
- National Key Research and Develop-ment Program of China [2021YFD1700102]
- Fundamental Research Funds for the Central Universities [JCQY202107]
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An attractive, versatile, and operationally simple visible-light-induced trifluoromethylation method has been demonstrated, which is transition-metal-free, photocatalyst-free, and oxidant-free. Inexpensive and readily available triflic anhydride (Tf2O) was chosen as the radical trifluoromethyl source, and thianthrene was used as a recyclable Tf2O-activating reagent, achieving a high-yielding and scalable trifluoromethylation reaction. Density functional theory and mechanistic studies revealed that the reaction involves a free radical homolytic process excited by visible light, generating a key trifluoromethyl radical intermediate.
An attractive, versatile, and operationally simple, visible-light-induced, transition-metal-free, photocatalyst-free, and oxidant-free trifluoromethylation has been demonstrated. Triflic anhydride (Tf2O), being inexpensive and readily available, was chosen as the radical trifluoromethyl source. Thianthrene was used as a recyclable Tf2O-activating reagent, and a high-yielding and scalable trifluoromethylation reaction was achieved. Density functional theory and mechanistic studies showed that a free radical homolytic process excited by visible light is involved in this reaction, generating a key trifluoromethyl radical intermediate.
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