Suzuki–Miyaura coupling: 4-Chloroanisole → 4-Methoxy-4'-trifluoromethyl-biphenyl
20% yield, run at 60 °C for 2 hours, as recorded by experimental reaction archive. The written procedure is below. One of 180 recorded runs making this product; all of them are compared below.
verified record, 20% yield recorded, Not balanced as written, From experimental reaction archive
The atoms, from reactants to products
Reactants · 1/6
breakingformingbond order changesmapped atom that changes
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | 4-Chloroanisole | C₇H₇ClO | |
| Reactant | 4-(Trifluoromethyl)phenylboronic acid | C₇H₆BF₃O₂ | |
| Reagent | Water | H₂O | |
| Reagent | Potassium Phosphate, Tribasic | K₃O₄P | |
| Catalyst | Bis(1,5-cyclooctadiene)nickel | C₁₆H₂₄Ni | |
| Catalyst | PiPr3 | C₉H₂₁P | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Solvent | 1,4-Dioxane | C₄H₈O₂ | |
| Product | 4-Methoxy-4'-trifluoromethyl-biphenyl | C₁₄H₁₁F₃O | 20% |
Conditions
- Temperature
- 60 °C
- Duration
- 2 hours
Yield
- 20% of 4-Methoxy-4'-trifluoromethyl-biphenyl.
Every recorded run making this product
180 runs of this class made the same product. The 40 highest-yielding are listed; this page's run is among them.
| Reactants | Catalyst | Reagents | Solvent | Temp. | Time | Yield |
|---|---|---|---|---|---|---|
| 1-Chloro-4-(trifluoromethyl)benzene; (4-Methoxyphenyl)boronic acid | Bis(1,5-cyclooctadiene)nickel; NPh-Pyrrole-PCy2, CataCXiumPCy | Water; Potassium Phosphate, Tribasic | 4 × 1,4-Dioxane | 60 °C | 45 minutes | 91% |
| 4-Chloroanisole; 4-(Trifluoromethyl)phenylboronic acid | Bis(1,5-cyclooctadiene)nickel; PCyp(3,5-tBu2-Ph)2 | Water; Potassium Phosphate, Tribasic | 4 × 1,4-Dioxane | 60 °C | 2 hours | 90% |
| 1-Chloro-4-(trifluoromethyl)benzene; (4-Methoxyphenyl)boronic acid | Bis(1,5-cyclooctadiene)nickel; PCyp(3,5-Me2-Ph)2 | Water; Potassium Phosphate, Tribasic | 4 × 1,4-Dioxane | 60 °C | 45 minutes | 90% |
| 1-Chloro-4-(trifluoromethyl)benzene; (4-Methoxyphenyl)boronic acid | Bis(1,5-cyclooctadiene)nickel; N(2-OMe-Ph)-Pyrrole-PCy2, cataCXiumPOMeCy | Water; Potassium Phosphate, Tribasic | 4 × 1,4-Dioxane | 60 °C | 45 minutes | 90% |
| 1-Chloro-4-(trifluoromethyl)benzene; (4-Methoxyphenyl)boronic acid | Bis(1,5-cyclooctadiene)nickel; 2-(Dicyclohexylphosphino)biphenyl | Water; Potassium Phosphate, Tribasic | 4 × 1,4-Dioxane | 60 °C | 45 minutes | 89% |
| 4-Chloroanisole; 4-(Trifluoromethyl)phenylboronic acid | Bis(1,5-cyclooctadiene)nickel; NPh-Pyrrole-PCy2, CataCXiumPCy | Water; Potassium Phosphate, Tribasic | 4 × 1,4-Dioxane | 60 °C | 2 hours | 88% |
| 4-Chloroanisole; 4-(Trifluoromethyl)phenylboronic acid | Bis(1,5-cyclooctadiene)nickel; PPh(3,5-tBu2-Ph)2 | Water; Potassium Phosphate, Tribasic | 4 × 1,4-Dioxane | 60 °C | 2 hours | 87% |
| 1-Chloro-4-(trifluoromethyl)benzene; (4-Methoxyphenyl)boronic acid | Bis(1,5-cyclooctadiene)nickel; PPh(3,5-tBu2-Ph)2 | Water; Potassium Phosphate, Tribasic | 4 × 1,4-Dioxane | 60 °C | 45 minutes | 87% |
| 4-Chloroanisole; 4-(Trifluoromethyl)phenylboronic acid | Bis(1,5-cyclooctadiene)nickel; PCy(3,5-tBu2-Ph)2 | Water; Potassium Phosphate, Tribasic | 4 × 1,4-Dioxane | 60 °C | 2 hours | 86% |
| 1-Chloro-4-(trifluoromethyl)benzene; (4-Methoxyphenyl)boronic acid | Bis(1,5-cyclooctadiene)nickel; PCy(4-OMe-Ph)2 | Water; Potassium Phosphate, Tribasic | 4 × 1,4-Dioxane | 60 °C | 45 minutes | 86% |
| 1-Chloro-4-(trifluoromethyl)benzene; (4-Methoxyphenyl)boronic acid | Bis(1,5-cyclooctadiene)nickel; P(exo-norbornenyl)(3,5-tBu2-Ph)2 | Water; Potassium Phosphate, Tribasic | 4 × 1,4-Dioxane | 60 °C | 45 minutes | 86% |
| 1-Chloro-4-(trifluoromethyl)benzene; (4-Methoxyphenyl)boronic acid | Bis(1,5-cyclooctadiene)nickel; Tri-m-tolylphosphine | Water; Potassium Phosphate, Tribasic | 4 × 1,4-Dioxane | 60 °C | 45 minutes | 84% |
| 1-Chloro-4-(trifluoromethyl)benzene; (4-Methoxyphenyl)boronic acid | Bis(1,5-cyclooctadiene)nickel; PCy(3,5-tBu2-Ph)2 | Water; Potassium Phosphate, Tribasic | 4 × 1,4-Dioxane | 60 °C | 45 minutes | 83% |
| 1-Chloro-4-(trifluoromethyl)benzene; (4-Methoxyphenyl)boronic acid | Bis(1,5-cyclooctadiene)nickel; Phosphine, cyclohexyldiphenyl- | Water; Potassium Phosphate, Tribasic | 4 × 1,4-Dioxane | 60 °C | 45 minutes | 83% |
| 1-Chloro-4-(trifluoromethyl)benzene; (4-Methoxyphenyl)boronic acid | Bis(1,5-cyclooctadiene)nickel; N-Phenyl-2-(dicyclohexylphosphino)indol | Water; Potassium Phosphate, Tribasic | 4 × 1,4-Dioxane | 60 °C | 45 minutes | 83% |
| 1-Chloro-4-(trifluoromethyl)benzene; (4-Methoxyphenyl)boronic acid | Bis(1,5-cyclooctadiene)nickel; PCyp(3,5-tBu2-Ph)2 | Water; Potassium Phosphate, Tribasic | 4 × 1,4-Dioxane | 60 °C | 45 minutes | 80% |
| 1-Chloro-4-(trifluoromethyl)benzene; (4-Methoxyphenyl)boronic acid | Bis(1,5-cyclooctadiene)nickel; Phosphine, tris[3,5-bis(1,1-dimethylethyl)phenyl]- | Water; Potassium Phosphate, Tribasic | 4 × 1,4-Dioxane | 60 °C | 45 minutes | 80% |
| 4-Chloroanisole; 4-(Trifluoromethyl)phenylboronic acid | 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 | 78% |
| 1-Chloro-4-(trifluoromethyl)benzene; (4-Methoxyphenyl)boronic acid | Bis(1,5-cyclooctadiene)nickel; PtBu(3,5-tBu2-Ph)2 | Water; Potassium Phosphate, Tribasic | 4 × 1,4-Dioxane | 60 °C | 45 minutes | 78% |
| 1-Chloro-4-(trifluoromethyl)benzene; (4-Methoxyphenyl)boronic acid | Bis(1,5-cyclooctadiene)nickel; PCy2Ph | Water; Potassium Phosphate, Tribasic | 4 × 1,4-Dioxane | 60 °C | 45 minutes | 76% |
| 1-Chloro-4-(trifluoromethyl)benzene; (4-Methoxyphenyl)boronic acid | Bis(1,5-cyclooctadiene)nickel; Cy-PhenCarPhos | Water; Potassium Phosphate, Tribasic | 4 × 1,4-Dioxane | 60 °C | 45 minutes | 75% |
| 1-Chloro-4-(trifluoromethyl)benzene; (4-Methoxyphenyl)boronic acid | Bis(1,5-cyclooctadiene)nickel; PCyp2(4-OMe-Ph) | Water; Potassium Phosphate, Tribasic | 4 × 1,4-Dioxane | 60 °C | 45 minutes | 72% |
| 1-Chloro-4-(trifluoromethyl)benzene; (4-Methoxyphenyl)boronic acid | Bis(1,5-cyclooctadiene)nickel; PCH2Cyp(3,5-tBu2-Ph)2 | Water; Potassium Phosphate, Tribasic | 4 × 1,4-Dioxane | 60 °C | 45 minutes | 71% |
| 1-Chloro-4-(trifluoromethyl)benzene; (4-Methoxyphenyl)boronic acid | Bis(1,5-cyclooctadiene)nickel; PPh2oTol | Water; Potassium Phosphate, Tribasic | 4 × 1,4-Dioxane | 60 °C | 45 minutes | 70% |
| 1-Chloro-4-(trifluoromethyl)benzene; (4-Methoxyphenyl)boronic acid | Bis(1,5-cyclooctadiene)nickel; Tris(3-methoxyphenyl)phosphine | Water; Potassium Phosphate, Tribasic | 4 × 1,4-Dioxane | 60 °C | 45 minutes | 69% |
| 4-Chloroanisole; 4-(Trifluoromethyl)phenylboronic acid | Bis(1,5-cyclooctadiene)nickel; 2-(Dicyclohexylphosphino)biphenyl | Water; Potassium Phosphate, Tribasic | 4 × 1,4-Dioxane | 60 °C | 2 hours | 67% |
| 4-Chloroanisole; 4-(Trifluoromethyl)phenylboronic acid | Bis(1,5-cyclooctadiene)nickel; Tribenzylphosphine | Water; Potassium Phosphate, Tribasic | 4 × 1,4-Dioxane | 60 °C | 2 hours | 67% |
| 1-Chloro-4-(trifluoromethyl)benzene; (4-Methoxyphenyl)boronic acid | Bis(1,5-cyclooctadiene)nickel; 2'-Dicyclohexylphosphino-2,4,6-trimethoxybiphenyl | Water; Potassium Phosphate, Tribasic | 4 × 1,4-Dioxane | 60 °C | 45 minutes | 67% |
| 1-Chloro-4-(trifluoromethyl)benzene; (4-Methoxyphenyl)boronic acid | Bis(1,5-cyclooctadiene)nickel; Diphenyl-p-tolylphosphine | Water; Potassium Phosphate, Tribasic | 4 × 1,4-Dioxane | 60 °C | 45 minutes | 61% |
| 4-Chloroanisole; 4-(Trifluoromethyl)phenylboronic acid | Bis(1,5-cyclooctadiene)nickel; Tri-m-tolylphosphine | Water; Potassium Phosphate, Tribasic | 4 × 1,4-Dioxane | 60 °C | 2 hours | 60% |
| 1-Chloro-4-(trifluoromethyl)benzene; (4-Methoxyphenyl)boronic acid | Bis(1,5-cyclooctadiene)nickel; PCyp(3,5-Mes2-Ph)2 | Water; Potassium Phosphate, Tribasic | 4 × 1,4-Dioxane | 60 °C | 45 minutes | 60% |
| 1-Chloro-4-(trifluoromethyl)benzene; (4-Methoxyphenyl)boronic acid | Bis(1,5-cyclooctadiene)nickel; MePhos | Water; Potassium Phosphate, Tribasic | 4 × 1,4-Dioxane | 60 °C | 45 minutes | 59% |
| 4-Chloroanisole; 4-(Trifluoromethyl)phenylboronic acid | Bis(1,5-cyclooctadiene)nickel; PCy2(3,5-TRIP2-Ph) | Water; Potassium Phosphate, Tribasic | 4 × 1,4-Dioxane | 60 °C | 2 hours | 58% |
| 4-Chloroanisole; 4-(Trifluoromethyl)phenylboronic acid | Bis(1,5-cyclooctadiene)nickel; PCy(4-OMe-Ph)2 | Water; Potassium Phosphate, Tribasic | 4 × 1,4-Dioxane | 60 °C | 2 hours | 57% |
| 1-Chloro-4-(trifluoromethyl)benzene; (4-Methoxyphenyl)boronic acid | 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 | 45 minutes | 55% |
| 4-Chloroanisole; 4-(Trifluoromethyl)phenylboronic acid | Bis(1,5-cyclooctadiene)nickel; PCyp(3,5-Me2-Ph)2 | Water; Potassium Phosphate, Tribasic | 4 × 1,4-Dioxane | 60 °C | 2 hours | 54% |
| 4-Chloroanisole; 4-(Trifluoromethyl)phenylboronic acid | Bis(1,5-cyclooctadiene)nickel; PCyp(3,5-Mes2-Ph)2 | Water; Potassium Phosphate, Tribasic | 4 × 1,4-Dioxane | 60 °C | 2 hours | 54% |
| 4-Chloroanisole; 4-(Trifluoromethyl)phenylboronic acid | Bis(1,5-cyclooctadiene)nickel; N(2-OMe-Ph)-Pyrrole-PCy2, cataCXiumPOMeCy | Water; Potassium Phosphate, Tribasic | 4 × 1,4-Dioxane | 60 °C | 2 hours | 54% |
| 1-Chloro-4-(trifluoromethyl)benzene; (4-Methoxyphenyl)boronic acid | Bis(1,5-cyclooctadiene)nickel; PtBu2Me | Water; Potassium Phosphate, Tribasic | 4 × 1,4-Dioxane | 60 °C | 45 minutes | 54% |
| 1-Chloro-4-(trifluoromethyl)benzene; (4-Methoxyphenyl)boronic acid | Bis(1,5-cyclooctadiene)nickel; Tribenzylphosphine | Water; Potassium Phosphate, Tribasic | 4 × 1,4-Dioxane | 60 °C | 45 minutes | 54% |
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-211c61ccceb14d72a2a9314bf4d653ee). Open the source and check it against what is on this page.
experimental reaction archive record ord-211c61ccceb14d72a2a9314bf4d653ee from dataset "Ni-catalyzed Suzuki Miyaura cross-coupling" (doi: 10.26434/chemrxiv.14388557.v1). No atom mapping is provided by the source.
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
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