Abstract
This work demonstrates that the copper acetate promoted N-arylation of imides with boronic acids can be employed as a major method for the synthesis of N3 -aryl hydantoins.
Key words
arylations - imides - hydantoins - organoboron chemistry - organometallic reagents
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General Procedure : Imide (2.1 mmol), Cu(OAc)2 (2.0 mmol, 0.38 g), 4 Å molecular sieves (750 mg crushed in a mortar) and triarylbismuthane or arylboronic acid (2.5 mmol) were combined in a Schlenk flask (100 mL) and anhyd CH2 Cl2 (50 mL) and pyridine (0.2 mL) were added. The flask was flushed with pure oxygen for 5 min, sealed (glass stopper tightened with Teflon ring) and the reaction mixture stirred for 7 d (TLC monitor) during which time the blue colour of the Cu(OAc)2 turned green. The solution was filtered through celite and thoroughly extracted with CH2 Cl2 (3 × 50 mL) and EtOAc (3 × 50 mL). The solvent was re-moved in vacuo. The residue was mixed with, and impreg-nated on, silica gel, and then separated via flash column chromatography (hexane-EtOAc; 4:1 for phthalimide deri-vatives; 2:3 for succinimide and 5,5′-dimethylhydantoin derivatives).
