Versatile synthesis of tunable N,S-bridged-[1.1.1.1]-cyclophanes promoted by ester functions

Volodymyr Malytskyi (1) , Vinicius Demetrio Da Silva (1) , Olivier Siri (1) , Michel Giorgi (2) , Jean-Manuel Raimundo (1, 3)

1 CINaM - Centre Interdisciplinaire de Nanoscience de Marseille
2 AMU SPEC - Spectropôle - Aix Marseille Université
3 AMU POLYTECH - Polytech Marseille

We report herein a powerful and highly adaptable metal-free organic synthetic route to functionalized N,S-bridged-[1.1.1.1]-cyclophanes using an ester-promoted macrocyclisation step. The newly synthesized cyclophanes are obtained in good yields exhibiting (i) high solubility, allowing the possibility to enlarge the scope and chemistry for such macrocycles, (ii) a tunable cavity and (iii) orthogonal functional groups. (C) 2016 Elsevier Ltd. All rights reserved.

Mots clés: Organic synthesis; Macrocycles; SNAr; [1.1.1.1]-Cyclophanes

Domaines: Chimie; Chimie organique

Volodymyr Malytskyi, Vinicius Demetrio Da Silva, Olivier Siri, Michel Giorgi, Jean-Manuel Raimundo. Versatile synthesis of tunable N,S-bridged-[1.1.1.1]-cyclophanes promoted by ester functions. Tetrahedron, 2016, 72 (41), pp.6363-6367. ⟨10.1016/j.tet.2016.08.034⟩. ⟨hal-01459073⟩