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通过选择性的三重和σ C-C及C-H键裂解实现的含两个乙炔酮单元的铜催化偶联反应。

Cu-Catalyzed Coupling with Two Ynone Units by Selective Triple and Sigma C-C and C-H Bond Cleavages.

作者信息

Nan Jiang, Zhang Jiawen, Hu Yan, Wang Chao, Wang Tingting, Wang Weitao, Ma Yangmin, Szostak Michal

机构信息

Shaanxi Key Laboratory of Chemical Additives for Industry, College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology, Xi'an 710021, China.

Department of Chemistry, Rutgers University, Newark, New Jersey 07102, United States.

出版信息

Org Lett. 2021 Mar 5;23(5):1928-1933. doi: 10.1021/acs.orglett.1c00371. Epub 2021 Feb 11.

DOI:10.1021/acs.orglett.1c00371
PMID:33570962
Abstract

We report a new copper-catalyzed [2 + 2 + 1] annulation process through the selective cleavage of sigma and triple C-C and C-H bonds using two ynone units. This new methodology involves breaking multiple chemical bonds in a single operation, including C≡C, C-C, C-H, and N-O. These high-value adducts lead to a diverse collection of synthetically challenging trisubstituted indolizines by the simultaneous engagement of different bond-breaking events and show excellent fluorescence in green aqueous solutions.

摘要

我们报道了一种新的铜催化[2 + 2 + 1]环化反应过程,该过程通过使用两个炔酮单元选择性地裂解σ键、碳-碳三键和碳-氢键。这种新方法涉及在一次操作中打破多个化学键,包括C≡C、C-C、C-H和N-O键。这些高价值加合物通过同时发生不同的断键事件,生成了一系列合成上具有挑战性的三取代中氮茚,并在绿色水溶液中显示出优异的荧光性能。

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