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

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

Zhu, Xin-Qi; Yuan, Han; Sun, Qing; Zhou, Bo; Han, Xiao-Qin; Zhang, Zhi-Xin; Lu, Xin; Ye, Long-Wu

Green chemistry : an international journal and green chemistry resource : GC, 2018, Volume: 20, Issue: 18

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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.

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