Traceless Sulfone Linker for the Solid-Phase Organic Synthesis of 1-(E)-Styryl-4-substituted-1,2,3-triazoles

Abstract

A novel, facile, solid-phase, organic synthesis of 1-(E)-styryl-4-substituted-1,2,3-triazoles in good yields and purities via traceless sulfone linker has been developed. Key steps involved in this synthetic procedure include (i) sulfone alkylation of sulfinate resin with (2-azido-1-iodoethyl)benzene, (ii) [3 + 2] cycloaddition with terminal alkynes in the presence of CuI, and (iii) traceless product release by base-mediated elimination process.

GRAPHICAL ABSTRACT

Keywords:

• Click chemistry
• 1,4-disubstituted-1,2,3-triazole
• elimination reaction
• 1-(E)-styryl substituent
• solid-phase organic synthesis
• sulfone linker

ACKNOWLEDGMENTS

We gratefully acknowledge financial support from the National Natural Science Foundation of China (No. 21062007) and the Research Program of Jiangxi Province Department of Education (Nos. GJJ10385, GJJ10733, and GJJ11380).

Notes

^a Overall isolated yields based on polystyrene-supported sodium sulfinate 1 (2. 0 mmol /g).

^b Determined by HPLC of crude cleavage product (λ = 254 nm).