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

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 solu...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2012-10, Vol.10 (41), p.8200-8202
Main Authors: McNitt, Christopher D, Popik, Vladimir V
Format: Article
Language:English
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Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c2ob26581h