Catalyst-free strain-promoted alkyne-azide cycloaddition (SPAAC) has become increasingly popular ligation strategy in the areas of material functionalization, as well as immobilization and labeling of various substrates. Oxa-dibenzocyclooctynes (ODIBO) are readily prepared by the photochemical decarbonylation of corresponding cyclopropenones (photo-ODIBO). ODIBO is not only the most reactive cyclooctyne reported so far but it also shows dramatic increase in the rate of cycloaddition in neutral aqueous solutions. The cyclopropenone precursor of ODIBO is stabile towards heating up to 160�C and does not react with endogenous nucleophiles or organic azides. Photochemical generation of ODIBO is virtually instantaneous and allows for the spatial and temporal control of labeling and functionalization.

Photochemical generation of oxa-dibenzocyclooctyne (ODIBO) a highly reactive cyclooctyne for metal-free click ligations

245th National Meeting (2013)

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