Practical, modular, and general synthesis of 3-coumaranones through gold-catalyzed intermolecular alkyne oxidation strategy

Chao Shu; Rongfu Liu; Shuang Liu; Jian-Qiao Li; Yong-Fei Yu; Qiao He; Xin Lu; Long-Wu Ye

doi:10.1002/asia.201403032

Practical, modular, and general synthesis of 3-coumaranones through gold-catalyzed intermolecular alkyne oxidation strategy

Chem Asian J. 2015 Jan;10(1):91-5. doi: 10.1002/asia.201403032. Epub 2014 Oct 6.

Authors

Chao Shu¹, Rongfu Liu, Shuang Liu, Jian-Qiao Li, Yong-Fei Yu, Qiao He, Xin Lu, Long-Wu Ye

Affiliation

¹ State Key Laboratory for Physical Chemistry of Solid Surfaces, Key Laboratory for Chemical Biology of Fujian Province and Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005 (China), Fax: (+86) 592-218-5833.

PMID: 25287758
DOI: 10.1002/asia.201403032

Abstract

A gold-catalyzed intermolecular alkyne oxidation for the preparation of 3-coumaranones has been developed. Using 8-isopropylquinoline N-oxides as oxidants, the reactions of o-ethynylanisoles afford versatile 3-coumaranones in moderate to good isolated yields. The synthetic utility of this chemistry is also indicated by the synthesis of the natural product sulfuretin.

Keywords: alkynes; gold; heterocycles; homogeneous catalysis; oxidation.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes / chemistry*
Biological Products / chemical synthesis
Biological Products / chemistry
Catalysis
Coumarins / chemical synthesis
Coumarins / chemistry*
Crystallography, X-Ray
Cyclization
Gold / chemistry*
Molecular Conformation
Oxidation-Reduction

Substances

3-coumaranone
Alkynes
Biological Products
Coumarins
Gold