CpCo(III)-Catalyzed Annulations of 2‑Alkenylphenols with CO: Mild Access to Coumarin Derivatives

Cp*Co­(III)-catalyzed annulations of 2-alkenylphenols with CO for the synthesis of coumarin derivatives have been developed. The reaction features mild reaction conditions, broad substrate scope, and good functional group tolerance. Preliminary mechanistic studies were conducted, suggesting that C–H...

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Bibliographic Details
Published in:Organic letters 2015-11, Vol.17 (21), p.5404-5407
Main Authors: Liu, Xu-Ge, Zhang, Shang-Shi, Jiang, Chun-Yong, Wu, Jia-Qiang, Li, Qingjiang, Wang, Honggen
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Biological Products - chemical synthesis
Biological Products - chemistry
Catalysis
Cobalt - chemistry
Coumarins - chemical synthesis
Coumarins - chemistry
Molecular Structure
Phenols - chemistry
Umbelliferones - chemical synthesis
Umbelliferones - chemistry
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Summary:Cp*Co­(III)-catalyzed annulations of 2-alkenylphenols with CO for the synthesis of coumarin derivatives have been developed. The reaction features mild reaction conditions, broad substrate scope, and good functional group tolerance. Preliminary mechanistic studies were conducted, suggesting that C–H activation is the turnover limiting step. Furthermore, the efficiency of this reaction was demonstrated by the rapid total synthesis of three natural products herniarin, xanthyletin, and seselin.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b02728