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

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.

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.

Yb(OTf)3-catalyzed sp3 C-H functionalization of 2- and 4-methyl azaarenes has been developed for efficient synthesis of biologically important azaarene-substituted 3-hydroxy-2-oxindoles in one step. Moderate to good yields were obtained for various isatins and azaarenes.Figure optionsDownload as PowerPoint slide