1.
J Org Chem
; 83(17): 10089-10096, 2018 09 07.
Artigo
em Inglês
| MEDLINE
| ID: mdl-30044625
RESUMO
A pyridinium chlorochromate (PCC)-mediated facile oxidative dimerization of 3-arylbenzofuran-2-ones at ambient temperature was developed which undergo oxidative cleavage to 3-aryl-3-hydroxy-benzofuran-2-ones with PCC at elevated temperatures. Finally, direct oxidation of 3-arylbenzofuran-2-ones to 3-aryl-3-hydroxy-benzofuran-2-ones was realized using a combination of PCC (10 mol %) and 2.0 equiv of H5IO6. The synthesized 3-aryl-3-hydroxy-benzofuranones were further converted to corresponding 3-amido-3-aryl-benzofuranones in high yields by Ritter reaction. Thus, the present protocol provides a nonconventional approach to C-3 hydroxylation of 3-arylbenzofuranones via their dimer using a catalytic amount of inexpensive chromium(VI) oxidant.