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J Org Chem. 2016 Jun 03;81(11):4861-8. doi: 10.1021/acs.joc.6b00535. Epub 2016 May 17.

HOTf-Catalyzed, Solvent-Free Oxyarylation of Ynol Ethers and Thioethers.

The Journal of organic chemistry

Liang Hu, Qingwen Gui, Xiang Chen, Ze Tan, Gangguo Zhu

Affiliations

  1. State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University , Changsha 410082, P. R. China.
  2. Department of Chemistry, Zhejiang Normal University , 688 Yingbin Road, Jinhua 321004, China.

PMID: 27163354 DOI: 10.1021/acs.joc.6b00535

Abstract

A novel HOTf-catalyzed oxyarylation of ynol ethers and thioethers has been realized with aryl sulfoxides as the oxyarylating reagents, providing α-arylated esters or thioesters in good to excellent yields. Notably, all atoms of the starting materials were incorporated in the product (100% atom economy) and the reaction proceeded under very mild conditions. It was found that the reaction can be ran under air and that the best yields are obtained under solvent-free conditions.

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