可见光诱导的烯炔和多氟烷基卤环化合成含氟异喹啉酮  

Visible-Light-Induced Cyclization of 1,n-Enyne and Polyfluoroalkyl Halides Toward Halo-perfluorinated 2,4-Dihydroisoquinoline-2(1 H)-one

作　　者：王硕文[1] 刘缘 徐振华 曾蓉 陈义 唐石[1] WANG Shuowen;LIU Yuan;XU Zhenhua;ZENG Rong;CHEN Yi;TANG Shi(College of Chemistry and Chemical Engineering,Jishou University,Jishou,Hunan 416000,China)

机构地区：[1]吉首大学化学化工学院,武陵山民族药解析与创制湖南省工程实验室,湖南吉首416000

出　　处：《应用化学》2020年第4期424-432,共9页Chinese Journal of Applied Chemistry

基　　金：国家自然基金(21662013);湖南省吉首大学研究生科研创新项目(Jdy19)资助。

摘　　要：发展了一种可见光诱导的1,7-烯炔与全氟烷基卤串联原子转移自由基加成(ATRA)/环化合成含氟2,4-二氢异喹啉-2(1 H)-酮的反应。以多氟烷基碘或溴为自由基前体,面式-三(2-苯基吡啶)合铱(摩尔分数1%)为光敏剂,在5 W蓝光发光二极管(LED)照射下,多种苯桥联1,7-烯炔顺利发生串联(ATRA)/环化反应,以中等到优秀(62%~84%)的产率合成了一系列多氟化异喹啉酮衍生物。此合成方法反应条件温和、清洁、高效且底物适用范围广,为具有潜在药用价值的多氟化2,4-二氢异喹啉-2(1 H)-酮的合成提供新的途径。Visible light-induced reaction of 1,7-enyne with perfluoroalkyl halide through a tandem atom transfer radical addition(ATRA)/cyclization sequence,synthesizing fluorinated 2,4-dihydroisoquinoline-2(1 H)-one was developed.With polyfluoroalkyl iodine or bromine as the free radical precursor,fac-Ir(ppy)3(molar fraction 1%)as the photosensitizer,ATRA/cyclization reactions of various benzene-linked 1,7-enyne occurred successfully under 5 W blue light emitting diode(LED)irradiation.A series of polyfluorinated isoquinolone derivatives was synthesized in modorate to excellent yields(62%~84%).This highly efficient synthetic method is mild and clean,providing a new way for the synthesis of polyfluoride 2,4-dihydroisoquinoline-2(1 H)-ketone with potential medicinal value.

关 键 词：可见光诱导 原子转移自由基加成 2 4-二氢异喹啉-2(1 H)-酮 多氟烷基化 烯炔 

分 类 号：O622.6[理学—有机化学]