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

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.

SUBMITTER: McNitt CD

PROVIDER: S-EPMC5992911 | biostudies-literature | 2012 Oct

REPOSITORIES: biostudies-literature

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

McNitt Christopher D CD Popik Vladimir V VV

Organic & biomolecular chemistry 20121001 41

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. ...[more]

PMID: 22987146

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