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

28% 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 record28% yield recordedNot balanced as writtenFrom experimental reaction archive

Reagents, catalysts and solvents are in the table below.

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The atoms, from reactants to products

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

Role	Species	Formula	Yield
Reactant	4-Chloroanisole	C₇H₇ClO	—
Reactant	Phenylboronic Acid	C₆H₇BO₂	—
Reagent	Water	H₂O	—
Reagent	Potassium Phosphate, Tribasic	K₃O₄P	—
Catalyst	Bis(1,5-cyclooctadiene)nickel	C₁₆H₂₄Ni	—
Catalyst	PCy2(3,5-TRIP2-Ph)	C₄₈H₇₁P	—
Solvent	1,4-Dioxane	C₄H₈O₂	—
Solvent	1,4-Dioxane	C₄H₈O₂	—
Solvent	1,4-Dioxane	C₄H₈O₂	—
Solvent	1,4-Dioxane	C₄H₈O₂	—
Product	4-Methoxybiphenyl	C₁₃H₁₂O	28%

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

28% 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.

Catalyst	Reagents	Solvent	Temp.	Time	Yield
Bis(1,5-cyclooctadiene)nickel; 2-(Dicyclohexylphosphino)biphenyl	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	100%
Bis(1,5-cyclooctadiene)nickel; PPh(3,5-tBu2-Ph)2	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	71%
Bis(1,5-cyclooctadiene)nickel; NPh-Pyrrole-PCy2, CataCXiumPCy	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	67%
Bis(1,5-cyclooctadiene)nickel; Tri-m-tolylphosphine	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	67%
Bis(1,5-cyclooctadiene)nickel; Phosphine, tris[3,5-bis(1,1-dimethylethyl)phenyl]-	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	65%
Bis(1,5-cyclooctadiene)nickel; PCH2Cyp(3,5-tBu2-Ph)2	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	51%
Bis(1,5-cyclooctadiene)nickel; PCy(3,5-tBu2-Ph)2	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	48%
Bis(1,5-cyclooctadiene)nickel; Tribenzylphosphine	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	47%
Bis(1,5-cyclooctadiene)nickel; PCyp(3,5-tBu2-Ph)2	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	45%
Bis(1,5-cyclooctadiene)nickel; Diphenyl-p-tolylphosphine	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	43%
Bis(1,5-cyclooctadiene)nickel; P(exo-norbornenyl)(3,5-tBu2-Ph)2	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	43%
Bis(1,5-cyclooctadiene)nickel; PCyp(3,5-Mes2-Ph)2	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	43%
Bis(1,5-cyclooctadiene)nickel; Tris(3-methoxyphenyl)phosphine	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	42%
Bis(1,5-cyclooctadiene)nickel; PCyp(3,5-Me2-Ph)2	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	39%
Bis(1,5-cyclooctadiene)nickel; PCy2Ph	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	35%
Bis(1,5-cyclooctadiene)nickel; Phosphine, cyclohexyldiphenyl-	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	33%
Bis(1,5-cyclooctadiene)nickel; PCyp2(4-OMe-Ph)	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	33%
Bis(1,5-cyclooctadiene)nickel; PCy(4-OMe-Ph)2	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	32%
Bis(1,5-cyclooctadiene)nickel; PCy2(3,5-TRIP2-Ph)	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	28% (this run)
Bis(1,5-cyclooctadiene)nickel; PtBu(3,5-tBu2-Ph)2	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	27%
Bis(1,5-cyclooctadiene)nickel; N-Phenyl-2-(dicyclohexylphosphino)indol	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	25%
Bis(1,5-cyclooctadiene)nickel; Tricyclohexylphosphine	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	23%
Bis(1,5-cyclooctadiene)nickel; Tributylphosphine	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	23%
Bis(1,5-cyclooctadiene)nickel; P(3,5-tBu2-Ph)2(3,5-TRIP2-Ph)	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	23%
Bis(1,5-cyclooctadiene)nickel; Trioctylphosphine	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	23%
Bis(1,5-cyclooctadiene)nickel; PPh2oTol	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	23%
Bis(1,5-cyclooctadiene)nickel; PEt3	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	22%
Bis(1,5-cyclooctadiene)nickel; N(2-OMe-Ph)-Pyrrole-PCy2, cataCXiumPOMeCy	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	20%
Bis(1,5-cyclooctadiene)nickel; PCyp(9THPQ)2	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	19%
Bis(1,5-cyclooctadiene)nickel; PtBu2Me	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	15%
Bis(1,5-cyclooctadiene)nickel; PCyp3	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	15%
Bis(1,5-cyclooctadiene)nickel; PiPr3	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	13%
Bis(1,5-cyclooctadiene)nickel; Tris(3-fluorophenyl)phosphine	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	11%
Bis(1,5-cyclooctadiene)nickel; PCyp2(3,5-TRIP2-Ph)	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	11%
Bis(1,5-cyclooctadiene)nickel; PMe3	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	9%
Bis(1,5-cyclooctadiene)nickel; Tris(3-chlorophenyl)phosphine	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	9%
Bis(1,5-cyclooctadiene)nickel; PAd2nBu, CataCXium A	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	6%
Bis(1,5-cyclooctadiene)nickel; PCypMes(3,5-tBu2-Ph)	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	6%
Bis(1,5-cyclooctadiene)nickel; MePhos	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	6%
Bis(1,5-cyclooctadiene)nickel; PPh (4-(2,2-(CF3)2-F7pent)-Ph)2	Water; Potassium Phosphate, Tribasic	4 × 1,4-Dioxane	60 °C	2 hours	6%

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-a4879ea635be4c1092c9296f804ec083). Open the source and check it against what is on this page.

experimental reaction archive record ord-a4879ea635be4c1092c9296f804ec083 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.

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

The atoms, from reactants to products

What was in the flask

Conditions

Yield

Every recorded run making this product

Procedure

The source

How to read this record

Where to next

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