4.7 Article

Synthesis of Oxazoles by Tandem Cycloisomerization/Allylic Alkylation of Propargyl Amides with Allylic Alcohols: Zn(OTf)2 as π Acid and σ Acid Catalyst

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 24, Pages 12718-12724

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b02382

Keywords

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Funding

  1. Natural Science Foundation of China [21572118, JQ201505]
  2. Natural Science Foundation of Shandong province [21572118, JQ201505]
  3. China Postdoctoral Science Foundation
  4. Shandong University [2014JC008, 104.205.2.5]

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A Zn(OTf)(2)-catalyzed tandem cycloisomerization/allylic alkylation of N-(propargyl)arylamides and allylic alcohols to produce Oxazole derivatives has been successfully developed. The zinc catalyst served as pi acid and also sigma acid in this reaction. The target allylic oxazoles have been transformed into multisubstituted diene Structures, which are potential aggregation-induced emission active Optical materials.

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