The introduction of an endocyclic sulfur atom enables finetuning of the reactivity and stability of thiacycloalkynes for copper-free click chemistry. An array of thiacycloalkynes that combines the intracyclic sulfur with various activating and deactivating groups was prepared, and a highly reactive but stable thiacycloheptyne, TMTH, was identified. TMTH proved stable in biologically relevant media and was shown to react with azides on proteins. Thus, TMTH is a promising scaffold for bioorthogonal reagents for copper-free click chemistry.

Thiacycloalkynes for copper-free click chemistry

244th National Meeting (2012)

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