Xu Jijun, Li Yi, Zhu Xuanyu, Lv Shisong, Xu Yiming, Cheng Tanyu, Liu Guohua, Liu Rui
Joint Laboratory of International Cooperation of Resource Chemistry of Ministry of Education, Shanghai Frontiers Science Center of Biomimetic Catalysis, Shanghai Normal University, Shanghai 201418, China.
Org Lett. 2023 Aug 25;25(33):6211-6216. doi: 10.1021/acs.orglett.3c02419. Epub 2023 Aug 16.
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)]PF 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.
我们在此展示一种吡啶鎓掩蔽的烯醇，作为一个通用平台，在蓝光（455 nm）照射下，在Ir(dF(Me)ppy)]PF存在的情况下制备带有三氟甲基、二氟甲基和一氟甲基的酮。通过简单改变氟源，一步法就能轻松以中等到优异的产率制备α-三氟甲基酮、α-二氟甲基酮和α-一氟甲基酮，使其成为合成含氟酮的实用工具。此外，吡啶鎓掩蔽的烯醇还可扩展到磺酰基酮的合成。本方法的研究结果丰富了氟化学的方法库，可能在制药和农用化学品行业有潜在应用。
