Issue 24, 2009

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

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

Supplementary files

Article information

Article type
Paper
Submitted
12 Jun 2009
Accepted
16 Sep 2009
First published
09 Nov 2009

Org. Biomol. Chem., 2009,7, 5255-5258

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

K. Chenoweth, D. Chenoweth and W. A. Goddard III, Org. Biomol. Chem., 2009, 7, 5255 DOI: 10.1039/B911482C

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