title: Alkyne Ligation Handles: Propargylation of Hydroxyl, Sulfhydryl, Amino, and Carboxyl Groups via the Nicholas Reaction.
abstract: The Nicholas reaction has been applied to the installation of alkyne ligation handles. Acid-promoted propargylation of hydroxyl, sulfhydryl, amino, and carboxyl groups using dicobalt hexacarbonyl-stabilized propargylium ions is reported. This method is useful for introduction of propargyl groups into base-sensitive molecules, thereby expanding the toolbox of methods for the incorporation of alkynes for bio-orthogonal reactions. High-value molecules are used as the limiting reagent, and various propargylium ion precursors are compared.
authors: Department of Chemistry, University of Pittsburgh , Pittsburgh, Pennsylvania 15206, United States.
authors: Sarah M
authors: SM
authors: Wells
authors: Department of Medicinal Chemistry, University of Minnesota , Minneapolis, Minnesota 55455, United States.
authors: John C
authors: JC
authors: Widen
authors: Department of Medicinal Chemistry, University of Minnesota , Minneapolis, Minnesota 55455, United States.
authors: Daniel A
authors: DA
authors: Harki
authors: Department of Chemistry, University of Pittsburgh , Pittsburgh, Pennsylvania 15206, United States.
authors: Kay M
authors: KM
authors: Brummond
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002248:Carbon Monoxide / Q000737:chemistry*; D003035:Cobalt / Q000737:chemistry; D017665:Hydroxyl Radical / Q000737:chemistry*; D015394:Molecular Structure; D010293:Pargyline / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D011392:Proline / Q000031:analogs & derivatives / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D000480:Alkynes; D013438:Sulfhydryl Compounds; D017665:Hydroxyl Radical; D003035:Cobalt; D002248:Carbon Monoxide; D011392:Proline; D010293:Pargyline