Pyridinium-Masked Enol as a Precursor for Constructing Alpha-Fluoromethyl Ketones
Jijun Xu, Yi Li, Xuanyu Zhu, Shisong Lv, Yiming Xu, Tanyu Cheng, Guohua Liu, Rui Liu
Abstract
Jijun Xu, Yi Li, Xuanyu Zhu, Shisong Lv, Yiming Xu, Tanyu Cheng, Guohua Liu, Rui Liu
Abstract
We present herein a pyridinium-masked enol as a versatile platform to produce ketones bearing tri-, di-, and monofluoromethyl in the presence of [Ir(dF(Me)ppy)] 2 (dtbbpy)]PF 6 under blue light (455 nm) irradiation. By simply changing the F-source, α-trifluoromethyl ketones, α-difluoromethyl ketones, and α-monofluoromethyl ketones could be easily prepared in moderate to excellent yields in one step, making it a practical tool for the synthesis of fluorine-containing ketones. In addition, the pyridinium-masked enol could also be extended to the synthesis of sulfonyl ketones. The findings of the present protocol contribute to the arsenal of fluorine chemistry and might have potential applications in the pharmaceutical and agrochemical industries.
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We present herein a pyridinium-masked enol as a versatile platform to produce ketones bearing tri-, di-, and monofluoromethyl in the presence of [Ir(dF(Me)ppy)] 2 (dtbbpy)]PF 6 under blue light (455 nm) irradiation. By simply changing the F-source, α-trifluoromethyl ketones, α-difluoromethyl ketones, and α-monofluoromethyl ketones could be easily prepared in moderate to excellent yields in one step, making it a practical tool for the synthesis of fluorine-containing ketones. In addition, the pyridinium-masked enol could also be extended to the synthesis of sulfonyl ketones. The findings of the present protocol contribute to the arsenal of fluorine chemistry and might have potential applications in the pharmaceutical and agrochemical industries.
Key concepts: Pyridinium, Chemistry, Enol, Fluorine, Combinatorial chemistry, Organic chemistry, Medicinal chemistry, Catalysis