Buchwald–Hartwig phosphination: Diphenylphosphine → 3-(Diphenylphosphino)pyridine
Run for 22 hours, as recorded by experimental reaction archive. The written procedure is below. One of 96 recorded runs making this product; all of them are compared below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | Diphenylphosphine | C₁₂H₁₁P | |
| Reactant | 3-Bromopyridine | C₅H₄BrN | |
| Reagent | BINAP Pd G3 30 | C₅₇H₄₅NO₃P₂PdS | |
| 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-(Diphenylphosphino)pyridine | C₁₇H₁₄NP | |
| Product | 3-Bromopyridine | C₅H₄BrN | |
| Product | Diphenylphosphine | C₁₂H₁₁P | |
| Product | Biphenyl | C₁₂H₁₀ |
Conditions
- Duration
- 22 hours
Yield
Every recorded run making this product
96 runs of this class made the same product. The 40 highest-yielding are listed; this page's run is among them.
| Catalyst | Reagents | Solvent | Temp. | Time | Yield |
|---|---|---|---|---|---|
| BINAP Pd G3 30; 1,8-Diazabicyclo(5.4.0)undec-7-ene | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded | |
| BINAP Pd G3 30; MTBD 25 | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded | |
| BINAP Pd G3 30; BEMP 27 | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded | |
| BINAP Pd G3 30; 2-tert-Butyl-1,1,3,3-tetramethylguanidine | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded | |
| BINAP Pd G3 30; tert-Butylimino-tri(pyrrolidino)phosphorane | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded | |
| BINAP Pd G3 30; 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 | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded (this run) | |
| DPPF Pd G3 31; 1,8-Diazabicyclo(5.4.0)undec-7-ene | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded | |
| DPPF Pd G3 31; MTBD 25 | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded | |
| DPPF Pd G3 31; 2-tert-Butyl-1,1,3,3-tetramethylguanidine | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded | |
| DPPF Pd G3 31; BEMP 27 | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded | |
| DPPF Pd G3 31; tert-Butylimino-tri(pyrrolidino)phosphorane | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded | |
| DPPF Pd G3 31; 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 | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded | |
| XantPhos Pd G2 32; 1,8-Diazabicyclo(5.4.0)undec-7-ene | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded | |
| XantPhos Pd G2 32; MTBD 25 | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded | |
| XantPhos Pd G2 32; 2-tert-Butyl-1,1,3,3-tetramethylguanidine | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded | |
| XantPhos Pd G2 32; BEMP 27 | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded | |
| XantPhos Pd G2 32; tert-Butylimino-tri(pyrrolidino)phosphorane | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded | |
| XantPhos Pd G2 32; 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 | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded | |
| tBu3P Pd G2 33; 1,8-Diazabicyclo(5.4.0)undec-7-ene | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded | |
| tBu3P Pd G2 33; MTBD 25 | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded | |
| tBu3P Pd G2 33; 2-tert-Butyl-1,1,3,3-tetramethylguanidine | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded | |
| tBu3P Pd G2 33; BEMP 27 | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded | |
| tBu3P Pd G2 33; tert-Butylimino-tri(pyrrolidino)phosphorane | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded | |
| tBu3P Pd G2 33; 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 | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded | |
| PPA Pd G3 34; 1,8-Diazabicyclo(5.4.0)undec-7-ene | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded | |
| PPA Pd G3 34; MTBD 25 | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded | |
| PPA Pd G3 34; 2-tert-Butyl-1,1,3,3-tetramethylguanidine | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded | |
| PPA Pd G3 34; BEMP 27 | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded | |
| PPA Pd G3 34; tert-Butylimino-tri(pyrrolidino)phosphorane | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded | |
| PPA Pd G3 34; 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 | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded | |
| Aphos Pd G3 35; 1,8-Diazabicyclo(5.4.0)undec-7-ene | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded | |
| Aphos Pd G3 35; MTBD 25 | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded | |
| Aphos Pd G3 35; 2-tert-Butyl-1,1,3,3-tetramethylguanidine | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded | |
| Aphos Pd G3 35; BEMP 27 | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded | |
| Aphos Pd G3 35; tert-Butylimino-tri(pyrrolidino)phosphorane | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded | |
| Aphos Pd G3 35; 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 | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded | |
| Xphos Pd G3 36; 1,8-Diazabicyclo(5.4.0)undec-7-ene | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded | |
| Xphos Pd G3 36; MTBD 25 | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded | |
| Xphos Pd G3 36; 2-tert-Butyl-1,1,3,3-tetramethylguanidine | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded | |
| Xphos Pd G3 36; BEMP 27 | 4 × Dimethyl Sulfoxide | — | 22 hours | not recorded |
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-850f9673a38c41448bbdfc8fd6681ce1). Open the source and check it against what is on this page.
experimental reaction archive record ord-850f9673a38c41448bbdfc8fd6681ce1 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.
Where to next
More Buchwald–Hartwig phosphination records
Other runs of this class, one page per distinct transformation.
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