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We have developed a protocol for the auxillary directed C–H chlorination of phenol derivatives using catalytic amounts of palladium acetate that is amenable to the late-stage chlorination of diflufenican and estrone. The 2-pyridine group allows for a highly efficient palladium-catalyzed chlorination and sequential ortho C–H functionalization reaction of phenol derivatives to produce a variety of symmetrical and unsymmetrical 2,4,6-trisubstituted phenols.

Regioselective C–H chlorination: towards the sequential difunctionalization of phenol derivatives and late-stage chlorination of bioactive compounds