Copper-Catalyzed Three-Component Tandem Reaction of Alkynes, α-Diazo Esters, and TMSN3 to Access N-Substituted 1,2,3-Triazoles

Yufen Lv; Zhiwei Wang; Lianhui Song; Jindong Hao; Shuyun Zhu; Huilan Yue; Wei Wei; Dong Yi

doi:10.1021/acs.joc.3c02112

Copper-Catalyzed Three-Component Tandem Reaction of Alkynes, α-Diazo Esters, and TMSN₃ to Access N-Substituted 1,2,3-Triazoles

J Org Chem. 2023 Dec 15;88(24):17266-17273. doi: 10.1021/acs.joc.3c02112. Epub 2023 Dec 4.

Authors

Yufen Lv¹, Zhiwei Wang¹, Lianhui Song¹, Jindong Hao¹, Shuyun Zhu¹, Huilan Yue², Wei Wei¹, Dong Yi³

Affiliations

¹ Key Laboratory of Catalytic Conversion and Clean Energy in Universities of Shandong Province, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, Shandong, China.
² Qinghai Provincial Key Laboratory of Tibetan Medicine Research and Key Laboratory of Tibetan Medicine Research, Northwest Institute of Plateau Biology, Chinese Academy of Sciences, Qinghai 810008, China.
³ School of Pharmacy, Southwest Medical University, Luzhou 646000, Sichuan, P. R. China.

PMID: 38047963
DOI: 10.1021/acs.joc.3c02112

Abstract

An efficient copper-catalyzed three-component tandem reaction of alkynes, α-diazo esters, and TMSN₃ to construct triazoles has been developed. Through this strategy, a number of diverse N-substituted 1,2,3-triazoles were conveniently obtained in moderate to good yields from simple and readily available starting materials using K₂CO₃ as the base. The mechanism of the tandem Cu-catalyzed azide-alkyne cycloaddition (CuAAC) and Cu-carbenoid-participated C-N coupling reaction has been investigated.