Copper(I)-Catalyzed Interrupted Click Reaction: Synthesis of Diverse 5-Hetero-Functionalized Triazoles

Weiguo Wang; Xianglong Peng; Fang Wei; Chen-Ho Tung; Zhenghu Xu

doi:10.1002/anie.201509124

Copper(I)-Catalyzed Interrupted Click Reaction: Synthesis of Diverse 5-Hetero-Functionalized Triazoles

Angew Chem Int Ed Engl. 2016 Jan 11;55(2):649-53. doi: 10.1002/anie.201509124. Epub 2015 Nov 27.

Authors

Weiguo Wang¹, Xianglong Peng¹, Fang Wei¹, Chen-Ho Tung¹, Zhenghu Xu^{2

3}

Affiliations

¹ Key Lab for Colloid and Interface Chemistry of Education Ministry, Department of Chemistry, Shandong University, No. 27 South Shanda Road, Jinan, 250100 (China) http://opcl.sdu.edu.cn/Teacher.aspx?tid=4.
² Key Lab for Colloid and Interface Chemistry of Education Ministry, Department of Chemistry, Shandong University, No. 27 South Shanda Road, Jinan, 250100 (China) http://opcl.sdu.edu.cn/Teacher.aspx?tid=4. xuzh@sdu.edu.cn.
³ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032 (P.R. China). xuzh@sdu.edu.cn.

PMID: 26610884
DOI: 10.1002/anie.201509124

Abstract

The 5-heterofunctionalized triazoles are important scaffolds in bioactive compounds, but current click reactions (CuAAC) cannot produce these core structures. A copper(I)-catalyzed interrupted click reaction to access diverse 5-functionalized triazoles is reported. Various 5-amino-, thio-, and selenotriazoles were readily assembled in one step in high yields. The reaction proceeds under mild conditions with complete regioselectivity. It also features a broad substrate scope and good functional group compatibility.

Keywords: aminations; click reactions; sulfenylation; triazoles.

Publication types

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