title: The solid-phase Nicholas reaction: scope and limitations.
abstract: Two libraries of alpha-substituted alkynes has been prepared on solid phase using a sequential Sonogashira/Nicholas reaction approach. The scope of nucleophiles in the Nicholas reaction on solid phase has been investigated, including carbon, oxygen, nitrogen, sulfur, fluoride, and hydride nucleophiles. The conditions for the reaction sequence have been optimized in terms of Lewis acid, catalyst for the Sonogashira step, temperature, reaction time, and decomplexation method, enabling the five-step sequence to be performed in 1 day.
authors.affiliation: Department of Chemistry and Bioscience, Chalmers University of Technology, SE-41296 Göteborg, Sweden.
authors.forename: Natalie
authors.initials: N
authors.lastname: Gachkova
authors.forename: Johan
authors.initials: J
authors.lastname: Cassel
authors.forename: Stefanie
authors.initials: S
authors.lastname: Leue
authors.forename: Nina
authors.initials: N
authors.lastname: Kann
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis*; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D002626:Chemistry, Pharmaceutical; D020650:Combinatorial Chemistry Techniques; D005459:Fluorides / Q000737:chemistry; D006846:Hydrocarbons, Halogenated / Q000737:chemistry; D008956:Models, Chemical; D009584:Nitrogen / Q000737:chemistry; D010100:Oxygen / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D011930:Reaction Time; D012117:Resins, Synthetic / Q000737:chemistry; D013455:Sulfur / Q000737:chemistry; D013696:Temperature
chemical_list: D000480:Alkynes; D006846:Hydrocarbons, Halogenated; D012117:Resins, Synthetic; D010165:Palladium; D013455:Sulfur; D002244:Carbon; D009584:Nitrogen; D005459:Fluorides; D010100:Oxygen