Palladium-catalysed enolate arylation, record ord-80a3eadcdfb049a0b6de5db6888ca50f
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 | Diethyl Malonate | C₇H₁₂O₄ | |
| Reactant | 3-Bromopyridine | C₅H₄BrN | |
| Reagent | tBuXPhos Pd G3 42 | C₄₂H₅₈NO₃PPdS | |
| Reagent | 2,N'3,N'3,N3,N3,N'5,N'5,N5,N5-nonamethyl-2,4,6-triaza-3lambda5,5lambda5-diphosphaocta-3,5-diene-3,3,5,5-tetramine | C₁₂H₃₅N₇P₂ | |
| Solvent | Dimethyl Sulfoxide | C₂H₆OS | |
| Solvent | Dimethyl Sulfoxide | C₂H₆OS | |
| Solvent | Dimethyl Sulfoxide | C₂H₆OS | |
| Solvent | Dimethyl Sulfoxide | C₂H₆OS | |
| Product | Diethyl 2-(pyridin-3-yl)malonate | C₁₂H₁₅NO₄ | |
| Product | 3-Bromopyridine | C₅H₄BrN | |
| Product | Diethyl Malonate | C₇H₁₂O₄ | |
| Product | Biphenyl | C₁₂H₁₀ |
Conditions
- Duration
- 22 hours
Yield
Procedure
Copied from the source record, unedited
The Mosquito was used to combine the source plate solutions by multi-aspiration of 250 nL of each of the four reaction components and then to dose the resulting reaction mixture (1 uL) into a 1536-well plate
The source
This record comes from experimental reaction archive (ord-80a3eadcdfb049a0b6de5db6888ca50f). Open the source and check it against what is on this page.
experimental reaction archive record ord-80a3eadcdfb049a0b6de5db6888ca50f from dataset "HTE Pd-catalyzed cross-coupling screen" (doi: 10.1126/science.1259203). 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.