The triazolyl analogue of the trityl cation

Mohamed Oukessou (1, 2) , Yves Génisson (1) , Dounia El Arfaoui (1, 2) , Abdeslem Ben-Tama (2) , El Mestafa El Hadrami (2) , Rémi Chauvin (3, 1, 4)

1 SPCMIB - Synthèse et Physico-Chimie de Molécules d'Intérêt Biologique
2 USMBA - Université Sidi Mohamed Ben Abdellah
3 LCC - Laboratoire de chimie de coordination
4 UT3 - Université Toulouse III - Paul Sabatier

The formation of the tris(3-benzyl-triazol-5-yl)carbenium cation, a heterocyclic analogue of the trityl cation, from tris(3-benzyl-triazol-5-yl)methanol, itself generated by Cu(I)-catalyzed Huisgen reaction of benzyl azide with triethynylmethanol, in the presence of trifluoroacetic anhydride is evidenced through a selective SN1 reactivity with various O-, N-, S-, and C-nucleophiles, giving the corresponding triazolylmethane derivatives in moderate to high yields.

Mots clés: Carbenium; Trityl cation; Tris(1; 2; 3-triazolyl)methanol; Tris(triazolyl)methylium

Domaines: Chimie de coordination

Mohamed Oukessou, Yves Génisson, Dounia El Arfaoui, Abdeslem Ben-Tama, El Mestafa El Hadrami, et al.. The triazolyl analogue of the trityl cation. Tetrahedron Letters, 2013, 54 (33), pp.4362-4364. ⟨10.1016/j.tetlet.2013.05.138⟩. ⟨hal-02908472⟩