Benign catalysis with zinc: atom-economical and divergent synthesis of nitrogen heterocycles by formal [3 + 2] annulation of isoxazoles with ynol ethers

Herein, we disclose an efficient zinc-catalyzed formal [3 + 2] annulation of isoxazoles with ynol ethers under exceptionally mild reaction conditions, leading to the atom-economical and divergent synthesis of 2-alkoxyl 1 H -pyrroles and 3 H -pyrroles, respectively. Importantly, this zinc-catalyzed p...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2018, Vol.2 (18), p.4287-4291
Main Authors: Zhu, Xin-Qi, Yuan, Han, Sun, Qing, Zhou, Bo, Han, Xiao-Qin, Zhang, Zhi-Xin, Lu, Xin, Ye, Long-Wu
Format: Article
Language:English
Subjects:
Catalysis
catalytic activity
Chemical reactions
Chemical synthesis
Crystallography
Ethers
Green chemistry
heterocyclic nitrogen compounds
Organic chemistry
Platinum
Pyrroles
Reaction mechanisms
Zinc
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Summary:Herein, we disclose an efficient zinc-catalyzed formal [3 + 2] annulation of isoxazoles with ynol ethers under exceptionally mild reaction conditions, leading to the atom-economical and divergent synthesis of 2-alkoxyl 1 H -pyrroles and 3 H -pyrroles, respectively. Importantly, this zinc-catalyzed protocol demonstrates the dramatically divergent reactivity from the relevant platinum catalysis, where the formal [4 + 2] annulation of isoxazoles with ynol ethers was involved. In addition, theoretical calculations provide further evidence for the feasibility of the proposed reaction mechanism, especially the distinct selectivity. A zinc-catalyzed formal [3 + 2] annulation of isoxazoles with ynol ethers has been developed, leading to the atom-economical and divergent synthesis of 2-alkoxyl 1 H -pyrroles and 3 H -pyrroles, respectively.
ISSN:1463-9262
1463-9270
1463-9270
DOI:10.1039/c8gc02051e