Regioselective synthesis of multisubstituted 1,2,3-triazoles: moving beyond the copper-catalyzed azide-alkyne cycloaddition. 2016

Fang Wei, and Weiguo Wang, and Yudao Ma, and Chen-Ho Tung, and Zhenghu Xu
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.

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.

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