Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetone | HCID 180 | — |
| Reactant | Allyl Alcohol | HCID 7858 | — |
| Reactant | Tri-o-tolylphosphine | HCID 80271 | — |
| Reactant | 5-Bromo-2-nitroaniline | HCID 5314766 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Diisopropylethylamine | HCID 81531 | — |
| Product | HCID 59736875 | HCID 59736875 | 18.3% |
Reaction Steps
A solution of bromoarene 2 (1.544 g, 7.11 mmol) (or any haloarene of choice); tri-o-tolyl-phosphine (280 mg; 0.9 mmol) and trkdibenzylidene acetone)dipalladium(0) (280 mg; 0.3 mmol) in N,N-dimethylformamide (6 mL) and ethyl diisopropyl amine (3 mL) was treated with prop-2-en-1-ol (3 mL, 40 mmol) (or any alken-1-ol of choice, 6 eq.) and the solution was stirred at 120° C. for 3 h under nitrogen. The reaction mixture was concentrated under high vacuum and the residue was purified by flash chromatography (eluent 5% MeOH in dichloromethane) to afford the aldehyde 80 (253 mg, 18% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07868205B2 |
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| Source dataset | uspto-grants-2011_01 |
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| ORD ID | ord-46531cf331804d6badbde7637ca3970e |
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| Source note | uspto-grants-2011_01 |
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