title: New tetramethylthiepinium (TMTI) for copper-free click chemistry.
abstract: A new derivative of the strained 3,3,6,6-tetramethylthiacycloheptyne (TMTH) bearing a functional handle is reported. Following an optimized synthesis, the handle was introduced by mild alkylation of the sulphur atom. The resulting functionalized strained 4,5-didehydro-3,3,6,6-tetramethyl-2,3,6,7-tetrahydrothiepinium (TMTI) proved to be stable and underwent extremely fast [3+2] cycloaddition reaction with benzyl azide in both organic and aqueous solvents. The reaction was equally efficient in cell lysate and serum and therefore opens interesting prospects for chemical-biology applications.
authors.affiliation: Laboratory of Functional Chemo-Systems UMR 7199, 74 Route du, Rhin, 67401, Illkirch, France.
authors.forename: Mathias
authors.initials: M
authors.lastname: King
authors.forename: Rachid
authors.initials: R
authors.lastname: Baati
authors.forename: Alain
authors.initials: A
authors.lastname: Wagner
mesh_terms: D057930:Click Chemistry; D015394:Molecular Structure; D013452:Sulfonium Compounds / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D013452:Sulfonium Compounds