Triphenylphosphine as a Ligand for the Pd-Catalyzed Amination of Un­activated Aryl Chlorides with Anilines Promoted by Salicylaldimine

Abstract

An efficient and selective amination of unactivated aryl chlorides with anilines catalyzed by mixed ligand Pd catalytic system of Ph₃P–salicylaldimine has been developed for the preparation of diarylamines. The benzyne mechanism was ruled out based on experimental results.

Key words

amination reaction - aryl chloride - salicylaldimine - di-arylamine - triphenylphosphine

• References and Notes

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• 15 2,2′,4,6,6′-Pentamethyldiphenylamine (3q) Yield 88%; white solid; mp 82–84 °C. ¹H NMR (400 MHz, CDCl₃): δ = 2.00 (s, 12 H), 2.25 (s, 3 H), 4.71 (br, 1 H), 6.78–6.82 (m, 3 H), 6.95 (s, 1 H), 6.98 (s, 1 H)

For the amination reaction of aryl chlorides though the benzyne mechanism, see:
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