Decarboxylative cross-coupling: 4-Iodotoluene → tert-Butyl 2-(p-tolyl)pyrrolidine-1-carboxylate
78% 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 | 4-Iodotoluene | C₇H₇I | |
| Reactant | 1-[(Tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid | C₁₀H₁₇NO₄ | |
| 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 2-(p-tolyl)pyrrolidine-1-carboxylate | C₁₆H₂₃NO₂ | 78% |
Conditions
- Temperature
- 23 °C
- Duration
- 72 hours
- Light
- visible light
Yield
- 78% of tert-Butyl 2-(p-tolyl)pyrrolidine-1-carboxylate.
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.
- 4-(1-(tert-Butoxycarbonyl)pyrrolidin-2-yl)benzoic acid90%
- tert-Butyl 2-(4-acetylphenyl)pyrrolidine-1-carboxylate86%
- tert-Butyl 2-(2-methylpyridin-4-yl)pyrrolidine-1-carboxylate85%
- Tert-butyl 2-(4-chlorophenyl)pyrrolidine-1-carboxylate77%
- Tert-butyl 2-(4-cyano-3-fluorophenyl)pyrrolidine-1-carboxylate75%
- Tert-butyl 2-(4-methoxyphenyl)pyrrolidine-1-carboxylate74%
- 2-(4-Methyl-pyridin-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester67%
- tert-Butyl 2-(4-fluorophenyl)pyrrolidine-1-carboxylate65%
- Tert-butyl 2-(6-phenylpyrimidin-4-yl)pyrrolidine-1-carboxylate65%
- Tert-butyl 2-(5-fluoro-2-pyridinyl)pyrrolidine-1-carboxylate64%
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-42e2098904ab491e9a348d65f0dddb47). Open the source and check it against what is on this page.
experimental reaction archive record ord-42e2098904ab491e9a348d65f0dddb47 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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