A One-Pot Procedure for the Regiocontrolled Synthesis of Allyltriazoles via the Pd-Cu Bimetallic Catalyzed Three-Component Coupling Reaction of Nonactivated Terminal Alkynes, Allyl Carbonate, and Trimethylsilyl Azide

Shin Kamijo, Tetsuo Kin, Zhibao Huo, Yoshinori Yamamoto

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94 Citations (Scopus)

Abstract

A one-pot procedure for the regiocontrolled synthesis of both 2-allyl- and 1-allyl-1,2,3-triazoles via the three-component coupling (TCC) reaction between nonactivated terminal alkynes, allyl carbonate, and trimethylsilyl azide (TMSN3) under a palladium and copper bimetallic catalyst has been developed. To accomplish the regioselective synthesis of the allyltriazoles, proper choice of two different catalyst systems is needed. The combination of Pd2(dba)3·CHCl3-CuCl(PPh 3)3-P(OPh)3 catalyzes the formation of 2-allyl-1,2,3-triazoles, while the combination of Pd(OAc)2-CuBr 2-PPh3 promotes the formation of 1-allyl-1,2,3-triazoles. The cooperative activity of palladium and copper catalysts plays an important role in the present transformations. Most probably, the palladium catalyst works as a catalyst for generating reactive azide species, π-allylpalladium azide complex and allyl azide. The copper catalyst probably behaves as an activator of the C-C triple bond of the starting terminal alkynes by forming a copper-acetylide intermediate and thereby promotes the [3 + 2]-cycloaddition reaction between the reactive azide species and the copper-acetylide to form the triazole framework.

Original languageEnglish
Pages (from-to)2386-2393
Number of pages8
JournalJournal of Organic Chemistry
Volume69
Issue number7
DOIs
Publication statusPublished - 2004 Apr 2

ASJC Scopus subject areas

  • Organic Chemistry

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