Buchwald–Hartwig amination, record ord-6eea29be7d4b47c5893b1e243ef41836
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 | Iodobenzene | C₆H₅I | |
| Reactant | N,N-Dimethylethylenediamine | C₄H₁₂N₂ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Dimethylformamide | C₃H₇NO | |
| Product | N-(2-(Dimethylamino)ethyl)aniline | C₁₀H₁₆N₂ | 0% |
Conditions
- Temperature
- 100 °C
Yield
- 0% of N-(2-(Dimethylamino)ethyl)aniline.
Procedure
Copied from the source record, unedited
In a 50 mL round-bottomed flask (t=g) was unsym-Dimethylethylenediamine (1.080 mL, 9.80 mmol), Iodobenzene (0.549 mL, 4.90 mmol), and TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.449 g, 0.49 mmol)Cesium carbonate (2.396 g, 7.35 mmol) andCesium carbonate (2.396 g, 7.35 mmol) were added. in DMF (10 mL) ([VOLUME]) to give a brown suspension. Reaction stirred over night at 100°C. no reaction.
The source
This record comes from experimental reaction archive (ord-6eea29be7d4b47c5893b1e243ef41836). Open the source and check it against what is on this page.
experimental reaction archive record ord-6eea29be7d4b47c5893b1e243ef41836 from dataset "750 AstraZeneca ELN dataset" (url: https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471). 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.