Preprint Communication Version 1 This version is not peer-reviewed

Efficient Erbium-Catalyzed [3+2] Cycloaddition: Regioselective Synthesis of 1,5-Disubstituted 1,2,3-Triazoles

Version 1 : Received: 23 November 2018 / Approved: 26 November 2018 / Online: 26 November 2018 (05:17:46 CET)

How to cite: Maiuolo, L.; Russo, B.; Algieri, V.; Nardi, M.; Di Gioia, M.L.; Tallarida, M.A.; De Nino, A. Efficient Erbium-Catalyzed [3+2] Cycloaddition: Regioselective Synthesis of 1,5-Disubstituted 1,2,3-Triazoles. Preprints 2018, 2018110569 (doi: 10.20944/preprints201811.0569.v1). Maiuolo, L.; Russo, B.; Algieri, V.; Nardi, M.; Di Gioia, M.L.; Tallarida, M.A.; De Nino, A. Efficient Erbium-Catalyzed [3+2] Cycloaddition: Regioselective Synthesis of 1,5-Disubstituted 1,2,3-Triazoles. Preprints 2018, 2018110569 (doi: 10.20944/preprints201811.0569.v1).

Abstract

A simple procedure to obtain 1,5-disubstituted 1,2,3-triazoles, using the catalytic system erbium(III) trifluoromethanesulfonate, 1-methyl pyridinium trifluoromethanesulfonate and water is described. The reaction proceeds through an eliminative azide–olefin cycloaddition (EAOC) offering a highly regioselective approach and good yields (81–94%). The advantages of this method include simple operations of work-up and the ability of the catalytic system to be re-used five times without an evident loss in yield.

Subject Areas

triazoles; azides; 1,3-dipolar cycloaddition; EAOC

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