Selenium-π-Acid Catalyzed Oxidative Functionalization of Alkynes: Facile Access to Ynones and Multisubstituted Oxazoles,ACS Catalysis

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Selenium-π-Acid Catalyzed Oxidative Functionalization of Alkynes: Facile Access to Ynones and Multisubstituted Oxazoles
ACS Catalysis ( IF 11.3 ) Pub Date : 2018-06-19 00:00:00 , DOI: 10.1021/acscatal.8b01595
Lihao Liao ₁ , Hang Zhang ₁ , Xiaodan Zhao ₁

Affiliation

Unprecedented selenium-catalyzed propargylic oxidation of alkynes is disclosed. Various propargylphosphonates and 3-alkynoates were efficiently converted to valuable ynones via unusual C–C triple bond migration and deselenenylation at a vinyl carbon. By the strategies of tautomerization of enamine intermediate and S_N2 displacement, similar conditions were effective for the oxidative difunctionalization of ynamides to afford multisubstituted oxazoles with high regioselectivity. Mechanistic studies revealed these detailed processes.

中文翻译：

炔烃的硒-π-酸催化氧化功能化：轻松获得壬和多取代的恶唑。

公开了前所未有的硒催化炔烃的炔丙基氧化。各种炔丙基膦酸酯和3-链烷酸酯通过不寻常的CC三键迁移和乙烯基碳上的硒烯基化反应，有效地转化为有价值的炔酮。通过烯胺中间体的互变异构和S _N 2置换的策略，相似的条件对于乙酰胺的氧化双官能化有效，从而提供了具有高区域选择性的多取代恶唑。机理研究揭示了这些详细的过程。

更新日期：2018-06-19

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