Yb(OTf)3 催化的碳氢键活化 2-甲基氮杂芳烃对靛红的加成反应

doi:10.1016/S1872-2067(11)60414-2

催化学报 ›› 2012, Vol. 33 ›› Issue (10): 1636-1641.DOI: 10.1016/S1872-2067(11)60414-2

Yb(OTf)₃催化的碳氢键活化 2-甲基氮杂芳烃对靛红的加成反应

牛瑞1, 杨世迎1, 肖建2,a, 梁涛2, 李兴伟2,b

1中国海洋大学环境科学与工程学院海洋环境与生态教育部重点实验室, 山东青岛 266100; 2中国科学院大连化学物理研究所, 辽宁大连 116023

收稿日期:2012-05-15 修回日期:2012-06-01 出版日期:2012-09-28 发布日期:2012-09-28

Yb(OTf)₃-Catalyzed Addition of 2-Methyl Azaarenes to Isatins via C–H Functionalization

NIU Rui1, YANG Shiying1, XIAO Jian2,a, LIANG Tao2, LI Xingwei2,b

1Key Laboratory of Marine Environment and Ecology, Ministry of Education, College of Environmental Science and Engineering, Ocean University of China, Qingdao 266100, Shandong, China; 2Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China

Received:2012-05-15 Revised:2012-06-01 Online:2012-09-28 Published:2012-09-28

摘要/Abstract

摘要： 发展了 Yb(OTf)₃ 催化的碳氢键活化 2-甲基氮杂芳烃或 4-甲基氮杂芳烃对靛红的加成反应, 对不同靛红和氮杂芳烃都取得了较好的产率. 该方法能够一步快速合成具有重要生理活性的氮杂芳烃取代的 3-羟基-2-氧化吲哚类化合物, 同时该反应成功扩展了路易斯酸在 sp3 碳氢键活化中的应用.

关键词: 三氟甲磺酸镱, 路易斯酸, 加成反应, 3-羟基-2-氧化吲哚, 2-甲基氮杂芳烃

Abstract: 3-Substituted-3-hydroxy-2-oxindoles are rich in a range of biologically active natural products and pharmaceuticals and development of efficient methods to construct this key motif is of vital importance. Yb(OTf)₃-catalyzed addition of 2- or 4-methyl azaarenes to isatins via C–H functionalization was developed. Moderate to good yields were obtained for various isatins and azaarenes. This method provides rapid protocol for the synthesis of biologically important azaarene-substituted 3-hydroxy-2-oxindoles in one step. The success of this reaction expands the synthetic utility of Lewis acid in the catalytic functionalization of sp³ C–H bonds in organic synthesis.

Key words: ytterbium triflate, Lewis acid, addition, 3-hydroxy-2-oxindole, 2-methylazaarene

牛瑞, 杨世迎, 肖建, 梁涛, 李兴伟. Yb(OTf)₃催化的碳氢键活化 2-甲基氮杂芳烃对靛红的加成反应[J]. 催化学报, 2012, 33(10): 1636-1641.

NIU Rui, YANG Shi-Ying, XIAO Jian, LIANG Tao, LI Xing-Wei. Yb(OTf)₃-Catalyzed Addition of 2-Methyl Azaarenes to Isatins via C–H Functionalization[J]. Chinese Journal of Catalysis, 2012, 33(10): 1636-1641.

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Yb(OTf)₃催化的碳氢键活化 2-甲基氮杂芳烃对靛红的加成反应

Yb(OTf)₃-Catalyzed Addition of 2-Methyl Azaarenes to Isatins via C–H Functionalization

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