Buchwald–Hartwig thioetherification, record ord-fd563dafb9ff45c79cd73bd8d34b8ebf
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 | Thiophenol | C₆H₆S | |
| Reactant | 3-Bromopyridine | C₅H₄BrN | |
| Reagent | DTBPF Pd G3 38 | C₃₉H₅₇FeNO₃P₂PdS | |
| 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 | 3-(Phenylsulfanyl)pyridine | C₁₁H₉NS | |
| Product | 3-Bromopyridine | C₅H₄BrN | |
| Product | Thiophenol | C₆H₆S | |
| 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-fd563dafb9ff45c79cd73bd8d34b8ebf). Open the source and check it against what is on this page.
experimental reaction archive record ord-fd563dafb9ff45c79cd73bd8d34b8ebf 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.