A study of Pd(II) Cl2/CuCl catalysed Wacker reaction for the deprotection of prop-2-enyl and prop-1-enyl ethers

Article abstract of DOI:10.1016/S0040-4020(97)10198-3

Pd(II)Cl₂ (1 mole equivalent)/CuCl/DMF-H₂O/O₂/2h catalysed oxidation of various prop-2-enyl ethers 1a-12a is reported to result in the formation of Wacker ketones 1b,3b,5b,6b,9b,11b,12b (12-51%), hydrolysis products 2c,4c-7c,9c-12c (12-43%) and η₂-vinyl complexes of palladium chloride 2c,4c,7c,8c (52-94%) respectively. The corresponding prop-1-enyl ethers 2e,4e-12e under similar conditions react with a catalytic amount of Pd(II)Cl₂ (0.2 mole equivalent) rapidly (15-20 min.) to give exclusively hydroxy compounds 2c,4c-12c respectively in good yields (75-97%).