This report describes the development of two photocatalytic methods for the pyridination of electron rich arenes. First, an S N Ar-type reaction between aryl halides and pyridine is developed and optimized. This transformation affords selective substitution of C(sp 2 )− halogen over C(sp 2 )−OR bonds to afford arylpyridinium products under anaerobic conditions. Under complementary aerobic conditions, analogous substrates are shown to undergo oxidative C(sp 2 )−H pyridination.
This communication
presents a new preparation for complexes of
the general structure [CpRRhCl2]2 (CpR = a substituted cyclopentadienyl ligand). Using
isopropyl alcohol as the solvent in place of ethanol prevents the
formation of Rh-carbonyl side products during synthesis. This procedure
also affords higher yields of many [CpRRhCl2]2 derivatives with significantly shorter reaction times
in comparison to previous methods. This procedure is applied to a
variety of complexes bearing sterically diverse cyclopentadienyl ligands.
This manuscript describes the systematic development of pyridine-type ligands, which promote the Pd catalyzed, non-directed amination of benzene in combination with novel, hydroxylamine-based electrophilic amination reagents. DFT calculations and mechanistic experiments provide insights into the factors influencing the arene C–H amination protocol.
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