Three-Component Chemo-Selective Synthesis of N-(o-Alkenylaryl) Pyrazoles by Pyrazole Annulation and Rh-Catalyzed Chemo-Selective Aryl C–H Addition Cascade,The Journal of Organic Chemistry

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Three-Component Chemo-Selective Synthesis of N-(o-Alkenylaryl) Pyrazoles by Pyrazole Annulation and Rh-Catalyzed Chemo-Selective Aryl C–H Addition Cascade
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2023-05-31 , DOI: 10.1021/acs.joc.3c00526
Demao Chen ₁ , Liyun Zhou ₁ , Chengping Wen ₂ , Jie-Ping Wan _{1,

2}

Affiliation

By using readily available enaminones, aryl hydrazine hydrochlorides, and alkynes as starting materials, the chemo-selective three-component synthesis of atropisomeric N-(o-alkenylaryl) pyrazoles has been efficiently accessed with rhodium catalysis. Unlike Satoh–Miura reaction leading to the alkyne-based C–H benzannulation by using prior prepared N-phenyl pyrazoles and alkynes as substrates, this three-component protocol displays unprecedented selectivity of C–H alkenylation by blocking the second round metal alkenylation with the key protonation step in the presence of acids.

中文翻译：

通过吡唑成环和 Rh 催化化学选择性芳基 C–H 加成级联三组分化学选择性合成 N-(邻烯基芳基) 吡唑

通过使用容易获得的烯胺酮、芳基肼盐酸盐和炔烃作为起始原料，在铑催化下有效地实现了阻转异构体N- (邻烯基芳基)吡唑的化学选择性三组分合成。与通过使用先前制备的 N-苯基吡唑和炔烃作为底物导致基于炔烃的 C-H 苯并环化的 Satoh-Miura 反应不同，该三组分方案通过用在酸存在下的关键质子化步骤。

更新日期：2023-05-31

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