Use of an Air-Stable Cu(I)-NHC Catalyst for the Synthesis of Peptidotriazoles

Pierrick Bruyat (1) , Arnaud Gautier (2) , Ludovic Jean (1) , Pierre-Yves Renard (1)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
2 ICCF - Institut de Chimie de Clermont-Ferrand

We report the use of air-stable Cu(I)-NHC complex 4a as a catalyst for the efficient microwave-assisted synthesis of peptidotriazoles on solid phase. Compared with the usual conditions (CuI or CuSO4/NaAsc), catalyst 4a allowed the preparation of a series of peptidomimetic compounds containing a 1,2,3-triazole ring in their backbone without the oxidation of common side-chains. Overall, the peptidotriazoles were obtained in good yields (61–87%), in excellent purity (higher than 94%) and with low copper contamination

Domaines: Chimie

Pierrick Bruyat, Arnaud Gautier, Ludovic Jean, Pierre-Yves Renard. Use of an Air-Stable Cu(I)-NHC Catalyst for the Synthesis of Peptidotriazoles. Journal of Organic Chemistry, 2018, 83 (21), pp.13515-13522. ⟨10.1021/acs.joc.8b01490⟩. ⟨hal-01916360⟩