氮杂环卡宾-钯(Ⅱ)-1-甲基咪唑配合物催化苯并■唑与对甲苯磺酸芳酯的C—H键直接芳基化反应  

N-Heterocyclic Carbene-Palladium(Ⅱ)-1-methylimidazole Complex Catalyzed Direct C—H Bond Arylation of Benzoxazoles with Aryl Tosylates

作　　者：郑宛莹 刘青鲜 邵黎雄[1] ZHENG Wan-ying;LIU Qing-xian;SHAO Li-xiong(College of Chemistry and Materials Engineering,Wenzhou University,Wenzhou 325035,China)

机构地区：[1]温州大学化学与材料工程学院

出　　处：《化学试剂》2019年第6期559-565,共7页Chemical Reagents

基　　金：国家自然科学基金资助项目(21471115)

摘　　要：2-芳基苯并唑是一类非常重要的有机化合物。以氮杂环卡宾-钯(Ⅱ)-1-甲基咪唑[NHC-Pd(Ⅱ)-Im]配合物为催化剂,通过催化苯并唑与对甲苯磺酸芳酯的C—H键直接芳基化,高效合成了2-芳基苯并唑类化合物。使用0.05倍物质的量的NHC-Pd(Ⅱ)-Im配合物为催化剂,3.5倍物质的量的LiOtBu为碱,以甲苯为溶剂,不同取代基的苯并唑和对甲苯磺酸芳酯在130℃下反应12h,以71%~92%的收率得到相应的C—H键直接芳基化产物。2-Aryl benzoxazoles are very important organic compounds.2-Aryl benzoxazoles are frequently found in some active compounds in the area of biology,materials sciences and natural products.In this work,2-aryl benzoxazole compounds were synthesized by direct C-H bond arylation of benzoxazoles with aryl tosylates in the presence of N-heterocyclic carbene-palladium(Ⅱ)-1-methylimidazole[NHC-Pd(Ⅱ)-Im]complex.Using NHC-Pd(Ⅱ)-Im(5 mol%)as the catalyst,LiOtBu(350 mol%)as the base,a series of benzoxazoles and aryl tosylates were examined in toluene at 130℃for 12 h,giving the corresponding direct C-H bond arylation products in 71%~92%yields.

关 键 词：氮杂环卡宾钯配合物 苯并唑 对甲苯磺酸芳酯 C-H芳基化 

分 类 号：O621.3[理学—有机化学]