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Updated: Sep 12, 2025

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Ruthenium-Catalyzed Cycloaddition of Azides and Selenoalkynes with Built-in "Catch-and-Release" Functionality
Qiang Feng1, Yu Tan2, Liang Chen1
1Department of Chemistry and the Hong Kong Branch of Chinese National Engineering Research Centre for Tissue Restoration & Reconstruction, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, China.
Abstract:
Click reactions with a "catch-and-release" functionality featuring both cross-linking and bond cleavage may have unique biomedical applications. However, despite the high demand, such reactions are rarely known in the toolbox of biochemists. Herein we introduce a robust click reaction of selenoalkynes that not only facilitates mild cross-linking with azides but also permits exceptionally facile cleavage of the C─Se bond in the adducts. This highly efficient ruthenium-catalyzed protocol features high chemoselectivity and regioselectivity, mild conditions, broad substrate scope, and good tolerance of functional groups and solvents. The compatibility with air and water as well as biomolecules has been demonstrated in parallel with the "catch-and-release" functionality.
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