Regioselective synthesis of multisubstituted 1,2,3-triazoles: moving beyond the copper-catalyzed azide-alkyne cycloaddition

Fang Wei; Weiguo Wang; Yudao Ma; Chen-Ho Tung; Zhenghu Xu

doi:10.1039/c6cc06194j

Regioselective synthesis of multisubstituted 1,2,3-triazoles: moving beyond the copper-catalyzed azide-alkyne cycloaddition

Chem Commun (Camb). 2016 Dec 6;52(99):14188-14199. doi: 10.1039/c6cc06194j.

Authors

Fang Wei¹, Weiguo Wang¹, Yudao Ma¹, Chen-Ho Tung¹, Zhenghu Xu²

Affiliations

¹ Key Lab of Colloid and Interface Chemistry of Ministry of Education, School of Chemistry and Chemical Engineering, Shandong University, No. 27 South Shanda Road, Jinan, Shandong 250100, China. xuzh@sdu.edu.cn ydma@sdu.edu.cn.
² Key Lab of Colloid and Interface Chemistry of Ministry of Education, School of Chemistry and Chemical Engineering, Shandong University, No. 27 South Shanda Road, Jinan, Shandong 250100, China. xuzh@sdu.edu.cn ydma@sdu.edu.cn and State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. China.

PMID: 27711308
DOI: 10.1039/c6cc06194j

Abstract

Copper(i)-catalyzed azide-alkyne cycloaddition (CuAAC) is an essential "click chemistry" reaction that is widely used in chemical biology, medicinal chemistry and materials science. The CuAAC reaction of terminal alkynes provides a mild and efficient synthesis of 1,4-disubstituted 1,2,3-triazoles. However, the click reaction of internal alkynes with azides, giving trisubstituted triazoles, is very challenging. This feature article highlights the recent progress addressing this fundamental problem. Particular emphasis is on the current and emerging strategies to introduce functional groups to the C-5 position of triazoles in a regioselective manner.