title: Imidazole-1-sulfonyl azide-based diazo-transfer reaction for the preparation of azido solid supports for solid-phase synthesis.
abstract: An efficient, standard, mild, and copper-free imidazole-1-sulfonyl azide hydrochloride-based diazo-transfer method was implemented in a set of four resins that cover a broad range of hydrophobicity. The imidazole-1-sulfonyl azide hydrochloride is easily prepared/commercially available, stable upon storage at 4 °C, and proved to be a suitable alternative to triflyl azide for diazo-transfer reactions in amine functionalized resins. We have successfully applied the azido resins for the conjugation of a TFA-labile Wang-type linker using Click Chemistry.
authors.affiliation: Institute for Research in Biomedicine (IRB Barcelona) , 08028-Barcelona, Spain.
authors.forename: Vida
authors.initials: V
authors.lastname: Castro
authors.forename: Juan B
authors.initials: JB
authors.lastname: Blanco-Canosa
authors.forename: Hortensia
authors.initials: H
authors.lastname: Rodriguez
authors.forename: Fernando
authors.initials: F
authors.lastname: Albericio
mesh_terms: D000588:Amines / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D057930:Click Chemistry; D007093:Imidazoles / Q000737:chemistry*; D060327:Solid-Phase Synthesis Techniques; D013450:Sulfones / Q000737:chemistry*
chemical_list: D000588:Amines; D001386:Azides; D007093:Imidazoles; D013450:Sulfones; C580844:imidazole-1-sulfonyl azide; C523862:imidazole-1-sulfonyl azide hydrochloride