Decarboxylative cross-coupling of p-Bromoacetophenone
77% yield, run at 23 °C for 72 hours, as recorded by experimental reaction archive. The written procedure is below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | p-Bromoacetophenone | C₈H₇BrO | |
| Reactant | CC(C)(C)OC(=O)NC(CCC(=O)Oc1ccccc1)C(=O)O | C₁₆H₂₁NO₆ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 4,4'-Di-tert-butyl-2,2'-bipyridyl | C₁₈H₂₄N₂ | |
| Catalyst | Dichloronickel;1,2-dimethoxyethane | C₄H₁₀Cl₂NiO₂ | |
| Catalyst | Ir[dF(CF3)ppy]2(dtbbpy)PF6 | C₄₂H₃₄F₁₆IrN₄P | |
| Solvent | Dimethylformamide | C₃H₇NO | |
| Product | CC(=O)c1ccc(C(CCC(=O)Oc2ccccc2)NC(=O)OC(C)(C)C)cc1 | C₂₃H₂₇NO₅ | 77% |
Conditions
- Temperature
- 23 °C
- Duration
- 72 hours
- Light
- visible light
Yield
- 77% of the product.
Other recorded runs with the same starting material
No other run in the library makes this product. These runs of the same class start from one of the same reactants, which is the nearest company this record has.
- Benzyl 2-(4-acetylphenyl)pyrrolidine-1-carboxylate93%
- tert-butyl N-[1-(4-acetylphenyl)-3-methylbutyl]-N-methylcarbamate91%
- tert-Butyl 2-(4-acetylphenyl)pyrrolidine-1-carboxylate86%
- tert-butyl N-[1-(4-acetylphenyl)-3-methylsulfanylpropyl]carbamate83%
- Tert-butyl 2-(4-acetylphenyl)piperidine-1-carboxylate82%
- 1-[4-(Oxolan-2-yl)phenyl]ethanone82%
- tert-butyl N-[1-(4-acetylphenyl)-2-methylpropyl]carbamate72%
- Tert-butyl 3-(4-acetylphenyl)morpholine-4-carboxylate61%
Procedure
Copied from the source record, unedited
Prior to irradiation, the reaction mixture was degassed by bubbling argon for 20 minutes
The source
This record comes from experimental reaction archive (ord-0b453c3805b0490c9fffb6fb51128e7a). Open the source and check it against what is on this page.
experimental reaction archive record ord-0b453c3805b0490c9fffb6fb51128e7a from dataset "Coupling of α-carboxyl sp3-carbons with aryl halides" (doi: 10.1126/science.1255525). 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
More Decarboxylative cross-coupling records
Other runs of this class, one page per distinct transformation.
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Percent yield calculator
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