Octet

Octet / Reactions

Negishi Coupling

Negishi Coupling (Coupling). Starts from Aryl halide with R-ZnX (organozinc), Pd catalyst. Mechanism in 3 steps.

Coupling

Reaction details

Name

Negishi Coupling

Type

Coupling

Starting Material

c1ccccc1Br

Product

c1ccccc1CC

Reagents

  • R-ZnX (organozinc)

  • Pd catalyst

Mechanism
  1. Smiles

    c1ccccc1Br

    Description

    Aryl halide

  2. Smiles

    [Zn]CC

    Description

    Organozinc reagent

  3. Smiles

    c1ccccc1CC

    Description

    Ethylbenzene (C-C bond formed)

Tips

  1. Organozinc + Halide → Coupled product

  2. More functional group tolerant than Grignard

  3. Nobel Prize 2010 (Negishi)

  4. Works well for sp³-sp² coupling

Related Reactions

  • suzuki-coupling

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Reactions

Related Content

Reagents, conditions, stereochemistry and mechanism.

SN2 with Hydroxide

SN2 with Hydroxide (SN2 Substitution). Starts from Bromoethane with NaOH, KOH. Conditions: Polar aprotic solvent in DMSO, DMF, or acetone. Stereochemistry: Inversion of configuration (Walden inversion). Mechanism in 3 steps.

Substitution

SN2 with Cyanide

SN2 with Cyanide (SN2 Substitution). Starts from Iodoethane with NaCN, KCN. Conditions: Polar aprotic solvent in DMSO or DMF. Stereochemistry: Inversion of configuration. Mechanism in 3 steps.

Substitution

SN1 Solvolysis

SN1 Solvolysis (SN1 Substitution). Starts from Tertiary bromide with H₂O. Conditions: Polar protic solvent, heat in Water or aqueous ethanol. Stereochemistry: Loss of stereocontrol (planar carbocation attacked from either face → racemization if chiral center)...

Substitution

SN2 with Tosylate Leaving Group

SN2 with Tosylate Leaving Group (SN2 Substitution). Starts from Ethyl tosylate with NaN₃. Conditions: Polar aprotic solvent. Mechanism in 2 steps.

Substitution

SN2 with Azide

SN2 with Azide (SN2 Substitution). Starts from Alkyl bromide substrate with NaN₃. Conditions: Polar aprotic solvent. Mechanism in 2 steps.

Substitution

E2 Elimination

E2 Elimination (E2 Elimination). Starts from 2-Bromobutane with 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.. Mechanism in 3 steps.

Elimination

Study guides

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