Sandmeyer Reaction
The substitution of an aromatic amino group is possible via preparation of its diazonium salt and subsequent displacement with a nucleophile (Cl-, I-, CN-, RS-, HO-). Many Sandmeyer Reactions proceed under copper(I) catalysis, while the Sandmeyer-type reactions with thiols, water and potassium iodide don't require catalysis.
The Sandmeyer Reaction is a very important transformation in aromatic chemistry, because it can result in some substitution patterns that are not achievable by direct substitution.
Fluorination is possible by using the related Schiemann Reaction.
Mechanism of the Sandmeyer Reaction
Recent Literature
Catalytic Sandmeyer Bromination
Halo- and Azidodediazoniation of Arenediazonium Tetrafluoroborates with Trimethylsilyl Halides and Trimethylsilyl Azide and Sandmeyer-Type Bromodediazoniation with Cu(I)Br in [BMIM][PF6] Ionic Liquid
Unusually Stable, Versatile, and Pure Arenediazonium Tosylates: Their Preparation, Structures, and Synthetic Applicability
One-Pot, Metal-Free Conversion of Anilines to Aryl Bromides and Iodides
Sulfonic Acid Based Cation-Exchange Resin: A Novel Proton Source for One-Pot Diazotization-Iodination of Aromatic Amines in Water
A New, One-Step, Effective Protocol for the Iodination of Aromatic and Heterocyclic Compounds via Aprotic Diazotization of Amines
A Highly Efficient Cu-Catalyzed S-Transfer Reaction: From Amine to Sulfide
Methanol-Promoted Borylation of Arylamines: A Simple and Green Synthetic Method to Arylboronic Acids and Arylboronates
Sandmeyer Trifluoromethylation
Copper-Promoted Sandmeyer Trifluoromethylation Reaction
Metal-Free Aromatic Carbon-Phosphorus Bond Formation via a Sandmeyer-Type Reaction
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