Sandmeyer Reaction. The substitution of an aromatic amino group is possible via preparation of its diazonium salt and subsequent displacement with a. The Sandmeyer reaction is an organic reaction used to convert an aryl diazonium salt to an aryl halide using a copper(I) halide catalyst. The mechanism begins with a single electron transfer (SET) from the copper to the diazonium to form a neutral diaso radical and copper(II) halide. The Sandmeyer reaction is a versatile synthetic tool by which an amino group on an aromatic ring is replaced with a wide range of substituents by converting an amino group attached to an aromatic ring into a diazonium salt that can be transformed into several functional groups.


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Since the leaving group Sandmeyer reaction is thermodynamically very stable, these reactions are energetically favored. Those substitution reactions that are catalyzed by cuprous salts are known as Sandmeyer reactions.


Fluoride substitution occurs on sandmeyer reaction with BF4 —a reaction known as the Schiemann reaction. Stable diazonium tetrafluoroborate salts may be isolated, and on heating these lose nitrogen to sandmeyer reaction an arylfluoride product.

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The top reaction with hypophosphorus acid, H3PO2, is noteworthy because it achieves the reductive removal of an amino or nitro group. Unlike the nucleophilic substitution reactions, this reduction sandmeyer reaction proceeds by a radical mechanism.

These aryl diazonium substitution reactions significantly expand the sandmeyer reaction available for the synthesis of polysubstituted benzene derivatives. Consider the following options: The usual precursor to an aryl amine is the corresponding nitro compound.

A nitro substituent deactivates an aromatic ring and directs electrophilic substitution to meta locations.

Reduction of a nitro group to an amine may be achieved in several ways. The sandmeyer reaction character of an amine substituent may be attenuated by formation of an amide derivative reversibleor even changed to deactivating and meta-directing by sandmeyer reaction of a quaternary-ammonium salt irreversible.

The solvent of choice for the synthesis of aryl iodides is diiodomethane[10] [11] while for the synthesis of aryl bromidesbromoform is used.

Sandmeyer reaction ~

For the synthesis of aryl chlorideschloroform is the solvent of choice. This reaction displays motifs characteristic of the Sandmeyer reaction reaction. A key intermediate in the synthesis of the anti-psychotic drug, Fluanxolis synthesized by a cyanation through the Sandmeyer sandmeyer reaction.

This process of trifluoromethylation provides unique chemical properties with a wide variety of practical applications.


Particularly, pharmaceuticals with CF3 groups have enhanced metabolic stabilitylipophilicityand bioavailability. Sandmeyer-type trifluoromethylation reactions feature mild reaction conditions sandmeyer reaction greater functional group sandmeyer reaction relative to earlier methods of trifluoromethylation.

Due to its wide synthetic applicability, the Sandmeyer reaction is complementary to electrophilic aromatic substitution.