Copper-catalyzed multicomponent reaction: synthesis of 4-arylsulfonylimino-4,5-dihydrofuran derivatives

Yongjia Shang; Kai Ju; Xinwei He; Jinsong Hu; Shuyan Yu; Min Zhang; Kaisheng Liao; Lifen Wang; Ping Zhang

doi:10.1021/jo1010075

Copper-catalyzed multicomponent reaction: synthesis of 4-arylsulfonylimino-4,5-dihydrofuran derivatives

J Org Chem. 2010 Aug 20;75(16):5743-5. doi: 10.1021/jo1010075.

Authors

Yongjia Shang¹, Kai Ju, Xinwei He, Jinsong Hu, Shuyan Yu, Min Zhang, Kaisheng Liao, Lifen Wang, Ping Zhang

Affiliation

¹ Key Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Key Laboratory of Molecule-Based Materials, College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, People's Republic of China. shyj@mail.ahnu.edu.cn

PMID: 20704448
DOI: 10.1021/jo1010075

Abstract

A series of 4-arylsulfonylimino-4,5-dihydrofurans (14 examples) were efficiently synthesized in good to excellent yields by using the copper-catalyzed three-component reaction between sulfonyl azides, phenylacetylene, and beta-ketoesters in tetrahydrofuran (THF) at 40 degrees C for 8 h in the presence of triethylamine (TEA). A plausible mechanism for this process is proposed.

Publication types

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

MeSH terms

Catalysis
Copper / chemistry*
Furans / chemical synthesis*
Furans / chemistry
Iodides / chemistry*
Molecular Structure
Stereoisomerism

Substances

Furans
Iodides
Copper
cuprous iodide