Cyclooctyne-based reagents for uncatalyzed click chemistry: A computational survey?

Organic & Biomolecular Chemistry Pub Date: 2009-11-09 DOI: 10.1039/B911482C

Abstract

With the goal of identifying alkyne-like reagents for use in click chemistry, but without Cu catalysts, we used B3LYP density function theory (DFT) to investigate the trends in activation barriers for the 1,3-dipolar cycloadditions of azides with various cyclooctyne, dibenzocyclooctyne, and azacyclooctyne compounds. Based on these trends, we find monobenzocyclooctyne-based reagents that are predicted to have dramatically improved reactivity over currently employed reagents.

Graphical abstract: Cyclooctyne-based reagents for uncatalyzed click chemistry: A computational survey
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