Click Chemistry on Polymer Support: Synthesis of 1-Vinyl- and 1-Allyl-1,2,3-triazoles via Selenium Linker

Abstract

Polystyrene-supported 2-azidoethyl phenyl selenide and 3-azidopropyl phenyl selenide reagents have been developed and applied to the traceless solid-phase organic synthesis of 1-vinyl- and 1-allyl-1,2,3-triazoles by CuI-mediated azide–alkyne cycloadditions and subsequent cleavage from the polymer support through oxidation–elimination reaction with 30% hydrogen peroxide. The advantages of this method include straightforward operation, good yield and purity of the products, and good stability and lack of odor for the reagents.

GRAPHICAL ABSTRACT

Keywords:

• 1-Allyl-1,2,3-triazoles
• click chemistry
• oxidation–elimination
• resin-bound 2-azidoethyl phenyl selenide
• resin-bound 3-azidopropyl
• solid-phase organic synthesis
• 1-vinyl-1,2,3-triazoles

ACKNOWLEDGMENTS

We gratefully acknowledge financial support from the National Natural Science Foundation (NSF) of China (No. 21062007), the NSF of Jiangxi Province (No. 2009GZH0016), and the Research Program of Jiangxi Province Department of Education (Nos. GJJ10385 and GJJ11380).

Notes

^a Reaction conditions: resin 3a (1.0 mmol), phenyl acetylene (4.0 mmol), catalyst (5 mol %), solvent (15 mL), r.t.

^b Conversion was estimated based on an increase in weight of the resin 3a.

^c 1.0 equivalent of triethylamine was used.

^d 1.5 equivalent of triethylamine was used.

^e 1.5 equivalent of DIPEA was used.

^f 2.0 equivalent of DIPEA was used.

^g 5.0 mmol of phenyl acetylene and 1.5 equivalent of DIPEA were used.

^a Isolated yields were based on the azide loading of the resin 3.

^b Determined by HPLC of crude cleavage product.