Pd-Catalyzed Reaction of Sterically Hindered Hydrazones with Aryl Halides: Synthesis of Tetra-Substituted Olefins Related to iso-Combretastatin A4
Pd-Catalyzed Reaction of Sterically Hindered Hydrazones with Aryl Halides: Synthesis of Tetra-Substituted Olefins Related to iso-Combretastatin A4
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DOI：
10.1021/ol101639g
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发表时间：
2010-09-17
期刊：
影响因子：
5.2
通讯作者：
Alami, Mouad
中科院分区：
文献类型：
--
作者：
Brachet, Etienne;Hamze, Abdallah;Alami, Mouad
PdCl(2)(MeCN)(2) 与 dppp 结合被证明是一种强大而有效的催化剂，用于空间位阻的 N-芳基磺酰腙与芳基卤化物的偶联，从而以良好的产率提供灵活且收敛的与异考布他汀 A4 相关的四取代烯烃的途径。该新方案已成功应用于具有生物学意义的联苯异丙叉 4-吡啶 CYP17 抑制剂 12b 的正式合成。
PdCl(2)(MeCN)(2) in combination with dppp proved to be a powerful and efficient catalyst for the coupling of sterically hindered N-arylsulfonylhydrazones with aryl halides, thus providing a flexible and convergent access to tetrasubstituted olefins related to iso-combretastatin A4 in good yields. This new protocol has been applied successfully to the formal synthesis of biphenylisopropylidene 4-pyridine CYP17 inhibitor, 12b, of biological interest.