title: A Mild, Large-Scale Synthesis of 1,3-Cyclooctanedione: Expanding Access to Difluorinated Cyclooctyne for Copper-Free Click Chemistry.
abstract: We report the large-scale synthesis of 1,3-cyclooctanedione in five steps with 29% yield. This molecule is a synthetic precurser to difluorinated cyclooctyne, which participates in a bioorthogonal copper-free click reaction with azides. The final step demonstrates the first successful application of the Wacker-Tsuji oxidation to form a cyclic 1,3-dione.
authors.affiliation: Department of Chemical & Biological Engineering, University of Colorado, Boulder, CO 80309, USA.
authors.forename: Evan A
authors.initials: EA
authors.lastname: Sims
authors.forename: Cole A
authors.initials: CA
authors.lastname: Deforest
authors.forename: Kristi S
authors.initials: KS
authors.lastname: Anseth