title: A homologation approach to the synthesis of difluorinated cycloalkynes.
abstract: Difluorinated cyclooctynes are important reagents for labeling azido-biomolecules through copper-free click chemistry. Here, a safe, scalable synthesis of a difluorinated cyclooctyne is reported, which involves a key homologation/ring-expansion reaction. Sequential ring expansions were also employed to synthesize and study a novel difluorinated cyclononyne.
authors.affiliation: Department of Chemistry, University of California , Berkeley, California 94720, United States.
authors.forename: Ellen M
authors.initials: EM
authors.lastname: Sletten
authors.forename: Gabriela
authors.initials: G
authors.lastname: de Almeida
authors.forename: Carolyn R
authors.initials: CR
authors.lastname: Bertozzi
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D034242:Cyclooctanes / Q000737:chemistry; D003516:Cycloparaffins / Q000138:chemical synthesis* / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D000480:Alkynes; D034242:Cyclooctanes; D003516:Cycloparaffins; D006845:Hydrocarbons, Fluorinated