Microflow Fluorinations of Benzynes: Efficient Synthesis of Fluoroaromatic Compounds

被引:10
作者
Ikawa, Takashi [1 ]
Masuda, Shigeaki [1 ]
Akai, Shuji [1 ]
机构
[1] Osaka Univ, Grad Sch Pharmaceut Sci, 1-6 Yamadaoka, Suita, Osaka 5650871, Japan
关键词
benzyne; microflow reaction; aromatic fluorination; nonafluorobutanesulfonate; silyl group; tetrabutylammonium fluoride; REGIOSELECTIVE DIELS-ALDER; FLOW MICROREACTOR SYNTHESIS; DOMINO ARYNE PRECURSOR; FLASH CHEMISTRY; BOND FORMATION; NUCLEOPHILIC DEOXYFLUORINATION; CATALYZED FLUORINATION; CONCISE SYNTHESIS; AR-F; GENERATION;
D O I
10.1248/cpb.c18-00578
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Fluorinated aromatic compounds are found in a variety of biologically active compounds, including clinical drugs and agrochemicals. Therefore, the synthesis of aryl fluorides is particularly important in the medicinal and process chemistry fields. In this paper, we report a method for the synthesis of aryl fluorides by benzyne fluorination under microflow conditions using the efficient Comet X-01 micromixer. In comparison to our previously reported method under ordinary batch conditions, this approach facilitates a significant reduction in reaction times, to ca. 10s, as well as increases in the yields of fluoroarenes (by up to 51%).
引用
收藏
页码:1153 / 1164
页数:12
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