Overview of 1,5-Selective Click Reaction of Azides with Alkynes or Their Synthetic Equivalents
Yaqi Zhao,
Zhengqi Chai,
Qingrui Zeng,
Wen-Xiong Zhang
Affiliations
Yaqi Zhao
Beijing National Laboratory for Molecular Sciences (BNLMS), State Key Laboratory of Rare-Earth Materials Chemistry and Applications, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China
Zhengqi Chai
Beijing National Laboratory for Molecular Sciences (BNLMS), State Key Laboratory of Rare-Earth Materials Chemistry and Applications, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China
Qingrui Zeng
Beijing National Laboratory for Molecular Sciences (BNLMS), State Key Laboratory of Rare-Earth Materials Chemistry and Applications, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China
Wen-Xiong Zhang
Beijing National Laboratory for Molecular Sciences (BNLMS), State Key Laboratory of Rare-Earth Materials Chemistry and Applications, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China
Nowadays, the click reaction of azides with alkynes has evolved rapidly and become one of the most efficient methods to synthesize 1,2,3-triazoles, which are an important class of N-containing heterocycles. While the 1,4-selective click reaction of azides with alkynes is well established to synthesize 1,4-substituted 1,2,3-triazoles, the corresponding 1,5-selective click reaction for the generation of 1,5-substituted-1,2,3-triazoles is much less explored, and there is no systematic review for the 1,5-selective click reaction. This timely review summarizes the discovery and development of 1,5-selective click reactions of azides with alkynes for the synthesis of 1,5-substituted 1,2,3-triazoles. The 1,5-selective click reactions will be divided into three types according to the critical reactive intermediates: metallacyclic intermediates, acetylide intermediate, and formal 1,5-selective azide-alkyne cycloaddition. The related mechanistic studies will also be involved in this review.
