文章摘要
赵鹏达,倪珊梅,周琢强.可见光诱导8-氨基喹啉衍生物二氟烷基化反应[J].精细化工,2020,37(8):0
可见光诱导8-氨基喹啉衍生物二氟烷基化反应
Visible Light Induced Difluoroalkylation of 8-Aminoquinoline Derivatives
投稿时间:2020-02-18  修订日期:2020-04-13
DOI:
中文关键词: 8-氨基喹啉  二氟溴乙酸乙酯  碘化亚铜  光诱导反应
英文关键词: 8-aminoquinoline  ethyl bromodifluoroacetate  cuprous iodide  light induced reaction
基金项目:
作者单位E-mail
赵鹏达 华南农业大学 zpd253@stu.scau.edu.cn 
倪珊梅 揭阳职业技术学院  
周琢强 华南农业大学 zqzhou@scau.edu.cn 
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中文摘要:
      室温条件下,研究了铜催化可见光诱导8-氨基喹啉衍生物C5位二氟烷基化反应。以蓝色LED为光源,面式-三(2-苯基吡啶)合铱配合物〔fac-Ir(ppy)3〕为光敏剂,8-氨基喹啉衍生物与二氟溴乙酸乙酯产生的二氟乙酸乙酯自由基发生C—C偶联反应。在CuI催化下合成15个C5位二氟烷基化的8-氨基喹啉衍生物(Ⅲa~Ⅲo)。通过1HNMR、13CNMR、FTIR和HR-MS对产物的结构进行确证。8-氨基喹啉衍生物的转化率为50%~90%,反应收率范围为21%~58%。该反应条件温和,含有卤素、硫醚和氰基官能团的底物都能发生反应。自由基捕获剂2,2,6,6-四甲基哌啶-1-氧(TEMPO)能捕获到二氟乙酸乙酯自由基,验证该反应过程可能经过自由基单电子转移。
英文摘要:
      A copper-catalyzed visible light induced difluoroalkylation reaction of 8-aminoquinoline derivatives at the C5- position was developed at room temperature. The C—C coupling reaction between 8-aminoquinoline derivatives and free radicals of ethyl difluoroacetate produced by ethyl difluorobromoacetate was carried out with blue LED as light source, fac-Tris[2-(2-pyridinyl)phenyl] iridium(Ⅲ) complexes (fac-Ir(ppy)3) as photosensitizer. Fifteen difluoroalkylated 8-aminoquinoline derivatives (Ⅲa~Ⅲo) at the C5 position were synthesized in the presence of a catalytic amount of cuprous iodide. These products were characterized by 1HNMR, 13HNMR, FTIR, and HR-MS. The conversion rates of starting materials were50%~90%, and yields of products was in the range from 21% to 58%. The reaction conditions are mild, and the substrates containing halogen, thioether, and cyan functional groups can react. Free radical scavenger2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) could capture free radicals of ethyl difluoroacetate, indicating that the reaction process may undergo free radical single electron transfer.
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