光催化4-芳基戊-4-烯酸和苯乙烯的苯硫基二氟甲基化双官能团化反应  

Photoredox Catalyzed Phenylthiodifluoromethylation Bifunctionalization of 4-Arylpent-4-enoic Acid and Styrene

作　　者：余宝 朱瑶瑶 黄焰根 YU Bao;ZHU Yaoyao;HUANG Yangen(College of Chemistry and Chemical Engineering,Donghua University,Shanghai 201620,China)

机构地区：[1]东华大学化学与化工学院,上海201620

出　　处：《合成化学》2024年第11期981-991,共11页Chinese Journal of Synthetic Chemistry

基　　金：国家自然科学基金资助项目(21677094)。

摘　　要：含芳基硫二氟甲基(ArSCF_(2))的化合物已被应用在药物和材料科学领域,开发ArSCF_(2)取代化合物的合成策略以满足其应用需求具有重要意义。光催化条件下,以苯硫基二氟甲基三苯基季鏻盐为苯硫基二氟甲基源,经过自由基加成、氧化和亲核反应,4-芳基戊-4-烯酸可转化为苯硫基二氟甲基取代的γ-内酯化合物;苯乙烯则在发生苯硫基二氟甲基化的同时与含氧亲核试剂反应得到双官能团化产物。两类产物收率中等(42%~78%),其结构经^(1)H NMR、^(13)C NMR、^(19)F NMR、IR和HR-MS分析确证。Compounds containing arylthiodifluoromethyl(ArSCF_(2))have found applications with the realm of drug discovery and material sciences.It is significant to develop synthetic strategies for ArSCF_(2)containing compounds to meet their application requirements.In this paper,phenylthiodifluoromethyltriphenylphosphonium triflate was used as the phenylthiodifluoromethyl source under photocatalysis.4-Arylpent-4-enoic acids were converted into phenylthiodifluoromethyl substitutedγ-lactones via radical addition,oxidation and nucleophilic reaction,and styrene underwent phenylthiodifluorom-ethylation and nucleophilic reaction with oxygen-containing nucleophiles to afford bifunctionalized products.The yields of the two categories of products are moderate(42%~78%),and their structures were characterized by^(1)H NMR,^(13)C NMR,^(19)F NMR,IR and HR-MS analyses.

关 键 词：苯硫基二氟甲基化 4-芳基戊-4-烯酸 苯乙烯 含氟季鏻盐 γ-内酯 光催化 

分 类 号：O623.731[理学—有机化学] O623.83[理学—化学]