Organic reaction

Suzuki Coupling

Suzuki coupling, also called Suzuki-Miyaura coupling, forms carbon-carbon bonds between organoboron reagents and aryl or vinyl halides under palladium catalysis.

Suzuki coupling scheme: bromobenzene and phenylboronic acid with a palladium catalyst and base give biphenyl, with the new aryl–aryl bond highlighted
Suzuki coupling: bromobenzene and phenylboronic acid give biphenyl; the new aryl–aryl bond is highlighted.

Reaction Scheme

aryl halide + boronic acid -> biarylPd catalyst, base, often aqueous organic solvent.

Primary reaction SMILES: B(O)(O)c1ccccc1.Brc1ccccc1>>c1ccc(-c2ccccc2)cc1

Two Common Examples

Bromobenzene + phenylboronic acid

Forms biphenyl under Pd/base conditions.

Aryl bromide + heteroaryl boronic acid

Common in medicinal chemistry library synthesis.

MolDraw Use

Sketch the halide, boronic acid, catalyst, base, and coupled product for reports or retrosynthesis notes.

How It Works

Suzuki–Miyaura coupling joins an organoboron compound (usually an aryl boronic acid or boronate ester) with an aryl or vinyl halide using a palladium catalyst and a base. The cycle has three steps: oxidative addition of the halide to Pd(0), transmetalation in which the organic group moves from boron to palladium (assisted by the base), and reductive elimination that forms the new C–C bond and regenerates Pd(0).

Conditions and Scope

  • It is widely used to make biaryls, a common motif in pharmaceuticals and materials.
  • Boronic acids are generally air-stable, and the boron by-products are relatively easy to remove.
  • Typical bases include K2CO3, Na2CO3, or K3PO4; reactions often run in mixtures of an organic solvent and water.
  • Many functional groups are tolerated, including esters, ketones, and nitriles.

FAQ

Why is a base needed? It activates the boron species (forming a boronate) so transmetalation can occur. Example: bromobenzene + phenylboronic acid gives biphenyl. In MolDraw, draw both partners, a straight arrow with "Pd(PPh3)4, K2CO3" above it, and highlight the new C–C bond with a colour.

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