The solid-phase Nicholas reaction: scope and limitations.
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.
Gachkova
Natalie
N
Department of Chemistry and Bioscience, Chalmers University of Technology, SE-41296 Göteborg, Sweden.
Cassel
Johan
J
Leue
Stefanie
S
Kann
Nina
N
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
D000480:Alkynes; D006846:Hydrocarbons, Halogenated; D012117:Resins, Synthetic; D010165:Palladium; D013455:Sulfur; D002244:Carbon; D009584:Nitrogen; D005459:Fluorides; D010100:Oxygen