Orthogonal arylations of 5-vinyl-1,2,4-triazoles

TETRAHEDRON

卷:76

Article

Azzouni, Safa^1,2  Gaucher, Anne¹  Prim, Damien¹  Efrit, Mohamed Lotfi² 

[1] Univ Paris Saclay, Inst Lavoisier Versailles, UVSQ, CNRS, F-78035 Versailles, France

[2] Univ Tunis El Manar, Fac Sci Tunis, Lab Synth Organ & Heterocycl Select Evaluat Act B, LR17ES01, Campus Univ, Tunis 2092, Tunisia

关键词: 1,2,4-triazole;    C-C bond formation;    C-N bond formation;    Palladium;    Copper;   

DOI  :  10.1016/j.tet.2020.130954

来源: Elsevier

【 摘 要 】

The preparation of 1,3,5-trisubstituted 1,2,4-triazoles is described using selective orthogonal arylation sequences. Ligand free Pd-catalyzed arylation allowed installing various (het)aryl units exclusively at the vinyl fragment of N1 substituted or N1-H precursors. Successful double arylations starting from ortho, meta and para bisiodobenzenes led to extended bistriazolyl derivatives. In contrast, Cu-catalyzed arylation using pyridylmethylamine as the ligand, led to N1-arylated triazoles keeping intact the vinyl moiety. Arylation process was compatible with electron donating groups in ortho, meta and para positions and tolerated electron withdrawing groups with a lesser extent. The strategy is general and spread the molecular diversity at the triazole core. (C) 2020 Elsevier Ltd. All rights reserved.

【 授权许可】

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