Metal-free (diacetoxy)iodobenzene-mediated C(sp 2 )-H phenylselenation of imidazo[1,2-a]pyridines and imidazo[2,1-b]thiazoles using diphenyl diselenide has been developed. This protocol exhibits broad substrate scope with good to excellent yields of the phenyl selenation product of imidazoheterocycles under mild conditions in short reaction time.
Synthesis of 2,3-diaryl acrylic acid is accomplished using the Perkin reaction between aromatic aldehyde and variously substituted phenyl acetic acids in presence of acetic anhydride and triethylamine at reflux condition. The reaction of resulting 2,3-diaryl acrylic acids with (diacetoxyiodo)benzene and tetraethylammonium bromide in MeOH/H2O forms 2-bromo-1,2-dimethoxy-1,2-diarylethane in moderate to good yields. The structure of the synthesized products was characterized by FTIR, 1H, 13C NMR spectroscopy and mass spectrometry. This is an unusual reaction observed for α,β-unsaturated carboxylic acids under transition metal-free oxidative condition.
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