Copper-Catalyzed Cyclization of 2-Alkynylanilines to Give 2-Haloalkoxy-3-alkyl(aryl)quinolines

Dong Lu; Songhua Chen; Niu Tang; Shuang-Feng Yin; Nobuaki Kambe; Renhua Qiu

doi:10.1021/acs.orglett.2c04314

Copper-Catalyzed Cyclization of 2-Alkynylanilines to Give 2-Haloalkoxy-3-alkyl(aryl)quinolines

Org Lett. 2023 Feb 3;25(4):676-681. doi: 10.1021/acs.orglett.2c04314. Epub 2023 Jan 22.

Authors

Dong Lu¹, Songhua Chen¹, Niu Tang¹, Shuang-Feng Yin¹, Nobuaki Kambe^{1

2}, Renhua Qiu¹

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 Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.

PMID: 36682056
DOI: 10.1021/acs.orglett.2c04314

Abstract

Herein we describe a method to produce 2-haloalkoxy-3-substituted quinolines via the cyclization of 2-alkynylanilines with TMSCF₃ and THF. This synthetic method uses inexpensive and easy-to-handle TMSCF₃ and employs a commercially available CuI catalyst to transform a broad range of 2-alkynylanilines into versatile 2-difluoromethoxy-3-substituted quinolines and 2-iodoalkoxy-3-substituted quinolines with excellent chemoselectivity.