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Investigation of the Reactivity of 1-Azido-3-Iodobicyclo[1.1.1]pentane under “Click” Reaction Conditions

submitted on 09.10.2020, 21:34 and posted on 12.10.2020, 12:58 by Elisabeth Sitte, Brendan Twamley, nitika grover, Mathias O.. Senge
The bicyclo[1.1.1]pentane (BCP) unit exhibits special physical and chemical properties and is under scrutiny as a bioisostere in drug molecules. We employed methodologies for the synthesis of different BCP triazole building blocks from one precursor, 1-azido-3-iodobicyclo[1.1.1]pentane, by Cu(I)-catalyzed 1,3-dipolar cycloaddition (“click”) reactions and integrated cycloaddition-Sonogashira coupling reactions. Thereby, we accessed three classes of substituted BCP derivatives: 1,4-disubstituted triazoles, 5-iodo-1,4,5-trisubstituted triazoles and 5-alkynylated 1,4,5-trisubstituted triazoles. This gives entry to the synthesis of multiply substituted BCP triazoles either on a modular or a one-pot basis. These methodologies were further utilized for appending large chromophoric porphyrin moieties onto the BCP core.


Science Foundation Ireland (SFI IvP 13/IA/1894)

Sydney E. Auchinleck Foundation


Email Address of Submitting Author


Trinity College Dublin, The University of Dublin



ORCID For Submitting Author


Declaration of Conflict of Interest

The authors declare no conflict of interest.

Version Notes

Version 1.0