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Ortho-metalation of p-chloroanisole: A media study

1999; Elsevier BV; Volume: 40; Issue: 10 Linguagem: Inglês

10.1016/s0040-4039(99)00161-6

1873-3581

D. W. Slocum, Pascal D. C. Dıetzel,

Catalytic Cross-Coupling Reactions

As the chlorophenyl group is a pharmacophore, its stability toward metalation conditions in conjunction with the methoxy substituent was assessed. For p-chloroanisole metalation ortho to the methoxy group was achieved in high yield using increments of THF in cyclohexane; numerous other regimes afforded lower yields and a competing benzyne pathway.