Transition-metal-catalyzed process for the preparation of sterically hindered N-substituted alkoxy amines

A process for preparing a sterically hindered N-alkyloxyamine of formula I, II o III

• which comprises
• reacting a sterically hindered nitroxyl compound of formula IV, V or VI
• with a diazonium salt of an aromatic amine of formula VII
• in the presence of a transition-metal catalyst
• wherein
• X is —CH2—, —O—, —S— or —NR8— where R8 is hydrogen or alkyl of 1 to 12 carbon atoms,
• R6 and R7 are independently alkyl of 1 to 8 carbon atoms, or R6 and R7 together are tetramethylene or pentamethylene,
• R is hydrogen, alkyl of 1 to 18 carbon atoms, aralkyl of 7 to 15 carbon atoms, aryl of 6 to 10 carbon atoms, hydroxyl, carboxyl, amino, alkylamino of 1 to 18 carbon atoms, dialkylamino of 2 to 36 carbon atoms, oxo, alkylthio of 1 to 18 carbon atoms, alkoxy of 1 to 18 carbon atoms, aryloxy of 7 to 15 carbon atoms, alkylcarbonyloxy of 2 to 18 carbon atoms or alkylcarbonylamino of 2 to 18 carbon atoms,
• G1 to G4 are independently hydrogen, halogen, nitro, cyano, alkyl of 1 to 18 carbon atoms, aralkyl of 7 to 15 carbon atoms, aryl of 6 to 10 carbon atoms, hydroxyl, carboxyl, alkylthio of 1 to 18 carbon atoms, alkoxy of 1 to 18 carbon atoms, aryloxy of 7 to 15 carbon atoms, alkylcarbonyloxy of 1 to 18 carbon atoms, alkylsulfonyl of 1 to 18 carbon atoms, arylsulfonyl of 6 to 15 carbon atoms, sulfo or phosphono, or any two vicinal substituents connected together form a mono or polycyclic ring, and
• G5 to G9 are independently hydrogen, alkyl of 1 to 18 carbon atoms, aralkyl of 7 to 15 carbon atoms or aryl of 6 to 10 carbon atoms.