Decarboxylative cross-coupling, record ord-5a3239d982264f8c8dc20d57d17e3036
One recorded run of this reaction. Below is what the source recorded, and nothing added to it.
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | p-Bromoacetophenone | C₈H₇BrO | |
| Reactant | Boc-Morph-OH | C₁₀H₁₇NO₅ | |
| 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 | Tert-butyl 3-(4-acetylphenyl)morpholine-4-carboxylate | C₁₇H₂₃NO₄ | 61% |
Conditions
- Temperature
- 23 °C
- Duration
- 72 hours
- Light
- visible light
Yield
- 61% of Tert-butyl 3-(4-acetylphenyl)morpholine-4-carboxylate.
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-5a3239d982264f8c8dc20d57d17e3036). Open the source and check it against what is on this page.
experimental reaction archive record ord-5a3239d982264f8c8dc20d57d17e3036 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.