Sc(OTf)_(3)催化的δ-三氟甲基-δ-芳基-双取代对亚甲基苯醌和硫醇的反应:高效合成二芳基甲烷硫醚化合物  

Sc(OTf)_(3)-Catalyzed 1,6-Conjugate Addition of Thiols to δ-CF_(3)-δ-aryl-disubstituted para-Quinone Methides:Efficient Construction of Diarylmethane Thioethers

作　　者：李华 庞靖祥[3] 刘华铮 赵长印 李松 王恒山 刘希功 Li Hua;Pang Jingxiang;Liu Huazheng;Zhao Changyin;Li Song;Wang Hengshan;Liu Xigong;无(State Key Laboratory,for Chemistry and Molecular Engineering of Medicinal Resources,Collaborative Innovation Center for Guangxi Ethnic Medicine,School of Chemistry and Pharmaceutical Sciences,Guangxi Normal University,Guilin 541004;School of Chemistry and Chemical Engineering,Shandong University,Jinan 250100;Shandong Medicinal Biotechnology Centre,Key Laboratory for Rare&Uncommon Diseases of Shandong Province,Key Lab for Biotech-Drugs of National Health Commission,Shandong First Medical University&Shandong Academy of Medical Sciences,Jinan 250000)

机构地区：[1]广西师范大学化学与药学学院药用资源化学与药物分子工程国家重点实验室广西民族医药协同创新中心,桂林541004 [2]山东大学化学与化工学院,济南250100 [3]山东第一医科大学药物研究所&山东省医学科学院,山东省医药生物技术中心,山东省罕见病重点实验室国家卫生委员会生物技术药物重点实验室,济南250000

出　　处：《有机化学》2021年第8期3134-3143,共10页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(Nos.21801093,21977021,81760626);中国博士后科学基金(No.2019M662321)资助项目.

摘　　要：报道了一种δ-三氟甲基-δ-芳基-二取代的对亚甲基苯醌和硫醇参与的1,6-共轭加成反应.在5 mol%三氟甲基磺酸钪催化的条件下,得到了结构多样化的含有三氟甲基四级碳中心的二芳基甲烷硫醚.反应具有良好的官能团兼容性和底物范围.此外,烷基硫醇和苄硫醇也适用于该反应.鉴于二芳基甲烷硫醚骨架以及三氟甲基在生物活性分子中的重要性,发展的含有三氟甲基取代四级碳中心的二芳基甲烷硫醚的高效合成方法将为生物活性分子的发现提供一条简洁、高效的策略.An efficient and practical 1,6-conjuate addition reaction of δ-CF_(3)-δ-aryl-disubstituted para-quinone methides with thiols has been described.This approach provides a straightforward access to structurally diverse diarylmethane thioethers bearing CF_(3)-substituted quaternary stereocenters using 5 mol% Sc(OTf)_(3) as catalyst.The reaction has an excellent function-al-group tolerance,and displays a broad scope with respect to both δ-CF_(3)-δ-aryl-disubstituted para-quinone methides and thi-ophenols.Moreover,alkyl thioalcohols and benzyl mercaptan have proven to be suitable substrates.Diarylmethane thioethers belong to an important structural scafFold that widely exists in a number of bioactive molecules and trifluoromethyl group has a profound effect on physiological properties of organic molecules.Therefore,the efficient method for the synthesis of diarylmethane thioethers bearing CF_(3)-substituted quaternary stereocenters might provide a powerful strategy for the discovery of biologically interesting agents.

关 键 词：δ-三氟甲基-δ-芳基-二取代 对亚甲基苯醌 二芳基甲烷 硫醚 1 6-共轭加成 

分 类 号：O625.72[理学—有机化学]