Issue 41, 2012
From the journal:

Organic & Biomolecular Chemistry

Photochemical generation of oxa-dibenzocyclooctyne (ODIBO) for metal-free click ligations†

Christopher D. McNitta  and  Vladimir V. Popik*a  

* Corresponding authors

a Department of Chemistry, University of Georgia, Athens, GA 30602, USA
E-mail: vpopik@uga.edu
Fax: +1 (706) 583-0342
Tel: +1 (706) 542-1953

Abstract

Oxa-dibenzocyclooctynes (ODIBO, 2a–c) are prepared by photochemical decarbonylation of corresponding cyclopropenones (photo-ODIBO, 1a–c). While photo-ODIBO does not react with azides, ODIBO is one of the most reactive cyclooctynes exhibiting rates of cycloaddition over 45 M−1 s−1 in aqueous solutions. ODIBO is stable under ambient conditions and has low reactivity towards thiols. Photo-ODIBO survives heating up to 160 °C and does not react with thiols.

Graphical abstract: Photochemical generation of oxa-dibenzocyclooctyne (ODIBO) for metal-free click ligations

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Article information

DOI
https://doi.org/10.1039/C2OB26581H
Article type
Communication
Submitted
09 Aug 2012
Accepted
28 Aug 2012
First published
31 Aug 2012

Org. Biomol. Chem., 2012,10, 8200-8202

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Photochemical generation of oxa-dibenzocyclooctyne (ODIBO) for metal-free click ligations

C. D. McNitt and V. V. Popik, Org. Biomol. Chem., 2012, 10, 8200 DOI: 10.1039/C2OB26581H

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