Cesium Fluoride and Copper‐Catalyzed One‐Pot Synthesis of Benzoxazoles via a Site‐Selective Amide C−N Bond Cleavage

We report herein a two‐step one‐pot strategy for the synthesis of benzoxazoles from amides by using cesium fluoride/copper as catalysts. This approach involves the in situ generation of acyl fluorides from the corresponding amides, and the acyl fluorides undergo transamidation and cyclization to giv...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2019-09, Vol.361 (17), p.4117-4125
Main Authors: Luo, Zhongfeng, Wu, Hongxiang, Li, Yue, Chen, Yuwen, Nie, Jingyi, Lu, Siqi, Zhu, Yulin, Zeng, Zhuo
Format: Article
Language:English
Subjects:
Acyl fluoride
Amides
Benzoxazoles
Cesium fluorides
Chemical synthesis
Copper
C−N bond
Fluorides
One-pot synthesis
Substrates
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Summary:We report herein a two‐step one‐pot strategy for the synthesis of benzoxazoles from amides by using cesium fluoride/copper as catalysts. This approach involves the in situ generation of acyl fluorides from the corresponding amides, and the acyl fluorides undergo transamidation and cyclization to give benzoxazoles in good yields. In this work, the amide C−N bonds are activated by CsF to form the acyl fluoride intermediates, which further react with o‐bromoanilines to efficiently yield benzoxazoles. Notably, this methodology demonstrates a broad substrate scope, as primary/secondary benzamides are well tolerated, and this process might facilitate the development of one‐pot transformations of amides.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201900485