Fluorous tagged N-hydroxy phthalimide for the parallel synthesis of O-aryloxyamines.
The parallel synthesis of O-aryloxyamines remains an unfulfilled need in the field of medicinal chemistry and fragment-based approaches. To fill this gap a solution-phase two-step process based on (1) a copper-catalyzed cross-coupling of aryl boronic acids with a fluorous tagged N-hydroxyphthalimide, and (2) a supported aminolysis was designed and optimized using Taguchi's method. A library of O-aryloxyamines was synthesized in high yields with high purity and diversity.
Gaucher-Wieczorek
Florence S
FS
Centre de recherches de Gif, Institut de Chimie des Substances Naturelles, UPR 2301-CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
Maillard
Ludovic T
LT
Badet
Bernard
B
Durand
Philippe
P
D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D001897:Boronic Acids / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003300:Copper / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D015394:Molecular Structure; D010797:Phthalimides / Q000737:chemistry*; D013237:Stereoisomerism
D000588:Amines; D001897:Boronic Acids; D006845:Hydrocarbons, Fluorinated; D010797:Phthalimides; D003300:Copper; C037437:N-hydroxyphthalimide