Cu(I)-Catalyzed Three-Component Reaction of Diazo Compound with Terminal Alkyne and Nitrosobenzene for the Synthesis of Trifluoromethyl Dihydroisoxazoles

Xinxin Lv; Zhenghui Kang; Dong Xing; Wenhao Hu

doi:10.1021/acs.orglett.8b01981

Cu(I)-Catalyzed Three-Component Reaction of Diazo Compound with Terminal Alkyne and Nitrosobenzene for the Synthesis of Trifluoromethyl Dihydroisoxazoles

Org Lett. 2018 Aug 17;20(16):4843-4847. doi: 10.1021/acs.orglett.8b01981. Epub 2018 Jul 27.

Authors

Xinxin Lv¹, Zhenghui Kang¹, Dong Xing¹, Wenhao Hu^{1

2}

Affiliations

¹ Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering , East China Normal University , 3663 North Zhongshan Road , Shanghai 200062 , China.
² School of Pharmaceutical Sciences , Sun Yat-sen University , Guangzhou 510006 , China.

PMID: 30052452
DOI: 10.1021/acs.orglett.8b01981

Abstract

A Cu(I)-catalyzed three-component reaction of terminal alkynes, trifluoromethyl diazo compounds, and nitrosoarenes was developed. With this method, a series of trifluoromethyl-substituted dihydroisoxazoles were effectively synthesized in high yields under mild reaction conditions. This transformation is proposed to proceed through an electrophilic trapping of the copper carbene species generated from terminal alkynes and diazo compounds by nitrosobenzenes.

Publication types

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