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

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-...

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Bibliographic Details
Published in:Journal of organic chemistry 2023-07, Vol.88 (13), p.8619-8627
Main Authors: Chen, Demao, Zhou, Liyun, Wen, Chengping, Wan, Jie-Ping
Format: Article
Language:English
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c00526