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Suzuki–Miyaura coupling: 4-Chloroanisole → 4-Methoxybiphenyl

19% yield, run at 60 °C for 2 hours, as recorded by experimental reaction archive. The written procedure is below. One of 90 recorded runs making this product; all of them are compared below.

verified record, 19% yield recorded, Not balanced as written, From experimental reaction archive

Reagents, catalysts and solvents are in the table below.

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The atoms, from reactants to products

COCCCCCCCCCCCCClOBO
Reactants · 1/6
breakingformingbond order changesmapped atom that changes

Drawn from the record's atom map: which bonds break and which form between the reactants and products the source listed. It shows a change in connectivity, not a simulated trajectory and not a mechanism.

What was in the flask

RoleSpeciesFormulaYield
Reactant4-ChloroanisoleC₇H₇ClO—
ReactantPhenylboronic AcidC₆H₇BO₂—
ReagentWaterH₂O—
ReagentPotassium Phosphate, TribasicK₃O₄P—
CatalystBis(1,5-cyclooctadiene)nickelC₁₆H₂₄Ni—
CatalystPCyp(9THPQ)2C₂₉H₃₇N₂P—
Solvent1,4-DioxaneC₄H₈O₂—
Solvent1,4-DioxaneC₄H₈O₂—
Solvent1,4-DioxaneC₄H₈O₂—
Solvent1,4-DioxaneC₄H₈O₂—
Product4-MethoxybiphenylC₁₃H₁₂O19%

The equation does not balance as written. That is usual for an experimental record: the source listed what it put in and what it measured, not a stoichiometric equation.

Conditions

Temperature
60 °C
Duration
2 hours

Only the dimensions the source stated are listed. Anything absent here was not recorded, and it is not inferred from what the class usually needs.

Yield

  • 19% of 4-Methoxybiphenyl.

Every recorded run making this product

90 runs of this class made the same product. The 40 highest-yielding are listed; this page's run is among them.

CatalystReagentsSolventTemp.TimeYield
Bis(1,5-cyclooctadiene)nickel; 2-(Dicyclohexylphosphino)biphenylWater; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours100%
Bis(1,5-cyclooctadiene)nickel; PPh(3,5-tBu2-Ph)2Water; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours71%
Bis(1,5-cyclooctadiene)nickel; NPh-Pyrrole-PCy2, CataCXiumPCyWater; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours67%
Bis(1,5-cyclooctadiene)nickel; Tri-m-tolylphosphineWater; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours67%
Bis(1,5-cyclooctadiene)nickel; Phosphine, tris[3,5-bis(1,1-dimethylethyl)phenyl]-Water; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours65%
Bis(1,5-cyclooctadiene)nickel; PCH2Cyp(3,5-tBu2-Ph)2Water; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours51%
Bis(1,5-cyclooctadiene)nickel; PCy(3,5-tBu2-Ph)2Water; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours48%
Bis(1,5-cyclooctadiene)nickel; TribenzylphosphineWater; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours47%
Bis(1,5-cyclooctadiene)nickel; PCyp(3,5-tBu2-Ph)2Water; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours45%
Bis(1,5-cyclooctadiene)nickel; Diphenyl-p-tolylphosphineWater; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours43%
Bis(1,5-cyclooctadiene)nickel; P(exo-norbornenyl)(3,5-tBu2-Ph)2Water; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours43%
Bis(1,5-cyclooctadiene)nickel; PCyp(3,5-Mes2-Ph)2Water; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours43%
Bis(1,5-cyclooctadiene)nickel; Tris(3-methoxyphenyl)phosphineWater; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours42%
Bis(1,5-cyclooctadiene)nickel; PCyp(3,5-Me2-Ph)2Water; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours39%
Bis(1,5-cyclooctadiene)nickel; PCy2PhWater; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours35%
Bis(1,5-cyclooctadiene)nickel; Phosphine, cyclohexyldiphenyl-Water; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours33%
Bis(1,5-cyclooctadiene)nickel; PCyp2(4-OMe-Ph)Water; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours33%
Bis(1,5-cyclooctadiene)nickel; PCy(4-OMe-Ph)2Water; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours32%
Bis(1,5-cyclooctadiene)nickel; PCy2(3,5-TRIP2-Ph)Water; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours28%
Bis(1,5-cyclooctadiene)nickel; PtBu(3,5-tBu2-Ph)2Water; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours27%
Bis(1,5-cyclooctadiene)nickel; N-Phenyl-2-(dicyclohexylphosphino)indolWater; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours25%
Bis(1,5-cyclooctadiene)nickel; TricyclohexylphosphineWater; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours23%
Bis(1,5-cyclooctadiene)nickel; TributylphosphineWater; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours23%
Bis(1,5-cyclooctadiene)nickel; P(3,5-tBu2-Ph)2(3,5-TRIP2-Ph)Water; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours23%
Bis(1,5-cyclooctadiene)nickel; TrioctylphosphineWater; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours23%
Bis(1,5-cyclooctadiene)nickel; PPh2oTolWater; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours23%
Bis(1,5-cyclooctadiene)nickel; PEt3Water; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours22%
Bis(1,5-cyclooctadiene)nickel; N(2-OMe-Ph)-Pyrrole-PCy2, cataCXiumPOMeCyWater; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours20%
Bis(1,5-cyclooctadiene)nickel; PCyp(9THPQ)2Water; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours19% (this run)
Bis(1,5-cyclooctadiene)nickel; PtBu2MeWater; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours15%
Bis(1,5-cyclooctadiene)nickel; PCyp3Water; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours15%
Bis(1,5-cyclooctadiene)nickel; PiPr3Water; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours13%
Bis(1,5-cyclooctadiene)nickel; Tris(3-fluorophenyl)phosphineWater; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours11%
Bis(1,5-cyclooctadiene)nickel; PCyp2(3,5-TRIP2-Ph)Water; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours11%
Bis(1,5-cyclooctadiene)nickel; PMe3Water; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours9%
Bis(1,5-cyclooctadiene)nickel; Tris(3-chlorophenyl)phosphineWater; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours9%
Bis(1,5-cyclooctadiene)nickel; PAd2nBu, CataCXium AWater; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours6%
Bis(1,5-cyclooctadiene)nickel; PCypMes(3,5-tBu2-Ph)Water; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours6%
Bis(1,5-cyclooctadiene)nickel; MePhosWater; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours6%
Bis(1,5-cyclooctadiene)nickel; PPh (4-(2,2-(CF3)2-F7pent)-Ph)2Water; Potassium Phosphate, Tribasic4 × 1,4-Dioxane60 °C2 hours6%

Every value is as the source recorded it. A run with no yield was reported without one, and nothing here is averaged, modelled or filled in.

Procedure

Copied from the source record, unedited

pre-ligate Ni(cod)2 and phosphine ligand in dioxane for 15 minutes in a separate plate

The source

This record comes from experimental reaction archive (ord-708d5f0db2694f38852eb94c0622e1f2). Open the source and check it against what is on this page.

  • experimental reaction archive record ord-708d5f0db2694f38852eb94c0622e1f2 from dataset "Ni-catalyzed Suzuki Miyaura cross-coupling" (doi: 10.26434/chemrxiv.14388557.v1). No atom mapping is provided by the source.

    experimental record · quality high · source

experimental reaction record.

How to read this record

This is one experiment, not a rule. It says that on one occasion these species were combined under these conditions and this came out. It does not say the reaction will give the same result on your substrate, and nothing on the page has been generalised into a claim that it would.

The pathway is a separate question, kept on separate pages. A mechanism here is the canonical arrow pushing for a class, run on real structures and labelled rule-derived. It is not evidence, and this record is not a mechanism.

Where to next

More Suzuki–Miyaura coupling records

Other runs of this class, one page per distinct transformation.

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