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

2009; Royal Society of Chemistry; Volume: 7; Issue: 24 Linguagem: Inglês

10.1039/b911482c

1477-0539

Kimberly Chenoweth, David M. Chenoweth, William A. Goddard,

Monoclonal and Polyclonal Antibodies Research

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.