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Suzuki-Miyaura Coupling

Suzuki-Miyaura Coupling (Coupling.) Converts c1ccccc1Br to c1ccccc1c2ccccc2 using PhB(OH)₂ (aryl boronic acid), Pd(PPh₃)₄, base (Na₂CO₃).

Coupling

Reaction details

Name

Suzuki-Miyaura Coupling

Type

Coupling

Starting Material

c1ccccc1Br

Product

c1ccccc1c2ccccc2

Reagents

  • PhB(OH)₂ (aryl boronic acid)

  • Pd(PPh₃)₄

  • base (Na₂CO₃)

Mechanism
  1. Smiles

    c1ccccc1Br

    Description

    Aryl halide (bromobenzene)

  2. Smiles

    c1ccc(B(O)O)cc1

    Description

    Phenylboronic acid (coupling partner)

  3. Smiles

    c1ccccc1c2ccccc2

    Description

    Biphenyl formed (Pd-catalyzed C-C bond formation)

Tips

  1. Most widely used cross-coupling reaction

  2. Boronic acids are air-stable, non-toxic

  3. Nobel Prize 2010 (Suzuki)

  4. Works with aryl, vinyl halides/triflates

Related Reactions

  • heck-reaction

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Reactions

Related Content

Source collection

SN2 with Hydroxide

SN2 with Hydroxide (SN2 Substitution.) Converts CCBr to CCO using NaOH, KOH. Conditions: Polar aprotic solvent in DMSO, DMF, or acetone. Stereochemistry: Inversion of configuration (Walden inversion).

Substitution

SN2 with Cyanide

SN2 with Cyanide (SN2 Substitution.) Converts CCI to CC#N using NaCN, KCN. Conditions: Polar aprotic solvent in DMSO or DMF. Stereochemistry: Inversion of configuration.

Substitution

SN1 Solvolysis

SN1 Solvolysis (SN1 Substitution.) Converts CC(C)(C)Br to CC(C)(C)O using H₂O. Conditions: Polar protic solvent, heat in Water or aqueous ethanol. Stereochemistry: Loss of stereocontrol (planar carbocation attacked from either face → racemization if chiral ce...

Substitution

SN2 with Tosylate Leaving Group

SN2 with Tosylate Leaving Group (SN2 Substitution.) Converts CCOS(=O)(=O)c1ccc(C)cc1 to CCN=[N+]=[N-] using NaN₃. Conditions: Polar aprotic solvent.

Substitution

SN2 with Azide

SN2 with Azide (SN2 Substitution.) Converts CCBr to CCN=[N+]=[N-] using NaN₃. Conditions: Polar aprotic solvent.

Substitution

E2 Elimination

E2 Elimination (E2 Elimination.) Converts CC(Br)CC to CC=CC using KOtBu, NaOEt, NaOH (conc.). Conditions: Strong base, heat in t-BuOH or EtOH. Stereochemistry: Anti-periplanar geometry required. E/Z depends on which H is removed..

Elimination

Study guides

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