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Palladium‐Catalyzed para‐C–H Arylation of Anilines with Aromatic Halides

Von Wiley-VCH zur Verfügung gestellt

Controlling regioselectivity in C–H functionalizations is a key challenge in chemical method development. In arenes, functionalizations are most difficult to direct towards the C–H group furthest away from a substituent, in its para position. We herein demonstrate how the para -C–H arylation of anilines with non-activated aryl halides, elusive to date, is achieved by a base-assisted “metalla-tautomerism” approach. A proton is abstracted from the aniline substrate and replaced by an arylpalladium species, generated from the aryl halide coupling partner. In this step, the palladium is directed away from the N - to the tautomeric para -C–H position by a large phosphine ligand combined with a triphenylmethyl shielding group. The triphenylmethyl group is easily installed and removed, and can be recycled.

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