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Deoxyfluorination of acyl fluorides to trifluoromethyl compounds by FLUOLEAD®/Olah’s reagent under solvent-free conditions
Beilstein Journal of Organic Chemistry ( IF 2.7 ) Pub Date : 2020-12-14 , DOI: 10.3762/bjoc.16.254
Yumeng Liang , Akihito Taya , Zhengyu Zhao , Norimichi Saito , Norio Shibata

A new protocol enabling the formation of trifluoromethyl compounds from acyl fluorides has been developed. The combination of FLUOLEAD® and Olah’s reagent in solvent-free conditions at 70 °C initiated the significant deoxyfluorination of the acyl fluorides and resulted in the corresponding trifluoromethyl products with high yields (up to 99%). This strategy showed a great tolerance for various acyl fluorides containing aryloyl, (heteroaryl)oyl, or aliphatic acyl moieties, providing good to excellent yields of the trifluoromethyl products. Synthetic drug-like molecules were also transformed into the corresponding trifluoromethyl compounds under the same reaction conditions. A reaction mechanism is proposed.

中文翻译:

FLUOLEAD®/ Olah's试剂在无溶剂条件下将酰基氟脱氧氟化为三氟甲基化合物

已经开发出一种新的方案,该方案能够从酰基氟形成三氟甲基化合物。FLUOLEAD的组合®和Olah试剂在不含溶剂的条件下在70℃开始的酰氟的显著deoxyfluorination并导致在相应的三氟甲基产品具有高的产率(高达99%)。该策略显示出对各种含有芳酰基,(杂芳基)酰基或脂族酰基部分的酰基氟的耐受性,从而提供了良好的至优异的三氟甲基产物收率。在相同的反应条件下,合成药物样分子也被转化为相应的三氟甲基化合物。提出了一种反应机理。
更新日期:2020-12-14
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