应用化学2018，Vol.35Issue(2)：181-188,8.DOI:10.11944/j.issn.1000-0518.2018.02.170099
可见光诱导烯烃去芳香化成环合成含氟氮杂螺环已二烯酮
Visible-Light-Induced Dearomatizing Spirocyclization of Alkenes Toward Perfluorinated Azaspirocyclic Cyclohexadienones
摘要
Abstract
A visible-light-induced dearomation cyclilation of N-benzylmethacrylamides with nonafluorinated alkyl bromides or iodides toward nonafluorinated azaspirocyclic cyclo-hexadienones was developed.Under the irradiation of blue light-emitting diode(LED)light, using fac-Ir(ppy)3(fac=facial, ppy=2-phenylpyridyl) as the photocatalyst, N-benzylmethacrylamides and nonafluorinated alkyl bromides or iodides underwent cascade dearomation/cyclilation under optimal conditions,leading to a series of perfluorinating azaspirocyclic cyclohexadienones in 61%~85% yield, as well as introducing a series of perfluorinated moieties including CF3,C3F7,C4F9, C6F13, C8F17, CH2CF2, CF2CO2Et(Et:Ethyl).Given the broad substrate scope, mild reaction conditions and green catalytic systems,this protocol provides a green,effective and quick approach to pharmaceutically important cyclohexadienones.关键词
多氟烷基化/去芳香化/环化/光催化/氮杂螺环已二烯酮Key words
perfluorinated/dearomative cyclilation/visible-light-induced/azaspirocyclic cyclohexadienones分类
化学化工引用本文复制引用
袁莉,唐石,李增增,蒋圣明,朱勇,雷千,夏绿露,李岚,余健,张娟..可见光诱导烯烃去芳香化成环合成含氟氮杂螺环已二烯酮[J].应用化学,2018,35(2):181-188,8.基金项目
国家自然基金资助项目(21462017,21662013),湖南省教育厅重点项目(16A171),湖南省研究生科研创新项目(CX2017B709)Supported by the National Natural Science Foundation of China(No.21462017,No.21662013),the Research Innovation Program for Graduates in Hu′nan province(No.16A171) （21462017,21662013）
