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When Hydrazonoyl Chlorides Meet Terminal Alkynes: Regioselective Copper(I)-Catalysed "Click" Sequential Reactions to 5-Substituted Pyrazoles
Heterocycles ( IF 0.8 ) Pub Date : 2020-06-05 , DOI: 10.3987/com-20-14268
Giorgio Molteni

In the presence of catalytic amounts of copper(I) salts, terminal alkynes underwent the formation of copper(I) acetylides that enabled their nucleophilic addition onto hydrazonoyl chlorides followed by spontaneous cyclisation of the resulting alkynylhydrazone intermediate. This sequential reaction sequence was exploited as a facile and regioselective synthesis of 1,3,5-substituted pyrazoles. A catalytic cycle has been proposed accounting for the observed results.

中文翻译:

当对羟基苯甲酰氯遇到末端炔烃:区域选择性铜(I)催化的“点击”顺序反应到5取代的吡唑。

在催化量的铜(I)盐的存在下,termina炔接受该启用他们的亲核加成到腙酰氯然后自然铜(I)乙炔化物的形成所产生的alkynylhydrazone中间的环化。此塞克Ñ TIA反应序列被利用作为简便和区域选择性合成ö ˚F 1,3,5-取代的吡唑。已经提出了考虑观察结果的催化循环。
更新日期:2020-06-05
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