摘要
烯烃双官能团化反应可将烯烃转化为多种重要的化合物,是一类十分重要的有机反应。实现了室温条件下光催化活化乙腈α位碳氢键,引发分子内官能团迁移的未活化烯烃双官能团化反应。以过氧化十二酰(LPO)为氢原子转移试剂,室温下经可见光催化,实现了乙腈转变为氰自由基,通过该自由基引发苯并噻唑基团的分子内迁移,实现了烯烃的双官能团化反应,将氰基和苯并噻唑同时引入未活化的烯烃末端双键的两端。采用核磁共振和质谱等波谱技术对目标产物进行了相应的表征,并对产物的特征核磁共振谱信号及可能的反应机理进行了分析。
The difunctionalization reaction of alkenes was a very important transformation for its conversion of olefins to a variety of important compounds.Difunctionalization reactions of inactivated alkenes by photocatalytic activation ofα-site C—H bond of acetonitrile and initiation of intramolecular functional group migration have been accomplished at room temperature.Using dodecyl peroxide(LPO)as hydrogen atom transfer reagent,acetonitrile was converted into cyanogen radical by visible light photocatalysis at room temperature.The bifunctional reaction of olefin was realized by the intramolecular migration of benzothiazole group initiated by the free radical.Cyano and benzothiazole were introduced into the two ends of inactive olefin terminal double bond at the same time.The target products were confirmed by 1HNMR,13CNMR and high resolution mass spectra(HRMS).The characteristic spectroscopic data of products was fully analyzed and the reaction mechanism is proposed.
作者
高俊
王杨丽
周烨
许甲喆
何永辉
GAO Jun;WANG Yang-li;ZHOU Ye;XU Jia-zhe;HE Yong-hui(Key Laboratory of Ethnic Medicine Resource Chemistry,State Ethnic Affairs Commission&Ministry of Education,Yunnan Minzu University,Kunming 650500,China)
出处
《化学试剂》
CAS
北大核心
2020年第8期1000-1003,共4页
Chemical Reagents
关键词
烯烃
光催化
双官能团化
有机合成
氰基
alkenes
photocatalysis
difunctionalization
organic synthesis
cyanophoric
