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Issue 74, 2012
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New tetramethylthiepinium (TMTI) for copper-free click chemistry

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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.

Graphical abstract: New tetramethylthiepinium (TMTI) for copper-free click chemistry

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Article information


Submitted
13 Jul 2012
Accepted
24 Jul 2012
First published
25 Jul 2012

Chem. Commun., 2012,48, 9308-9309
Article type
Communication

New tetramethylthiepinium (TMTI) for copper-free click chemistry

M. King, R. Baati and A. Wagner, Chem. Commun., 2012, 48, 9308
DOI: 10.1039/C2CC35034C

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