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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Synonyms: Bis(dibenzylideneacetone)palladium
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Palladium-catalyzed dearomative 1, 4-hydroamination
Gilbert, Robert ; Davis, Christopher W ; Bingham, Tanner W ; Sarlah, David ;
Abstract: A dearomative 1,4-hydroamination of nonactivated arenes has been developed, using a key arene-arenophile photocycloaddition strategy to disrupt aromaticity. Palladium catalysis with K-Selectride® as a hydride source uniquely enables selective reactivity and provides access to a range of substituted 1,4-cyclohexadienes from aromatic starting materials. We demonstrate a few synthetic applications of this scalable procedure by preparing highly-functionalized small molecules in three to four steps from naphthalene.
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Keywords: Dearomatization ; Hydroamination ; Arenophiles ; Palladium ; Catalysis
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Purchased from AmBeed: 32005-36-0 ; 657408-07-6 ; 787618-22-8 ; 213697-53-1 ; 12150-46-8
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CAS No. : | 32005-36-0 |
Formula : | C34H28O2Pd |
M.W : | 575.00 |
SMILES Code : | [Pd].C2=C(C=CC(C=CC1=CC=CC=C1)=O)C=CC=C2.C3=CC=CC=C3C=CC(C=CC4=CC=CC=C4)=O |
Synonyms : |
Bis(dibenzylideneacetone)palladium
|
MDL No. : | MFCD00051942 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H317 |
Precautionary Statements: | P261-P272-P280-P302+P352-P333+P313-P363-P403-P501 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With caesium carbonate; triphenylphosphine; In 1,4-dioxane; | Example 105 Under nitrogen atmosphere, to a mixture of <strong>[52333-42-3]7-bromopyrido[2,3-b]pyrazine</strong> (300 mg), methyl boronate (100 mg) and cesium carbonate (930 mg) were added dioxane (7.0 ml), bis(dibenzilidenacetone)-palladium (80.0 mg) and triphenylphosphine (87.0 mg), and the mixture was stirred at 100 C. for 2.5 hours. To the reaction solution was added a saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted three times with ethyl acetate. The extracts were combined, washed with a saturated brine, dried over magnesium sulfate, and filtered. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column (hexane/ethyl acetate=3/1?1/1?0/1?ethyl acetate/ethanol=10/1) to give 7-methyl-pyrido[2,3-b]pyrazine (125 mg, 60%). 1H NMR (CDCl3, 400 MHz) delta 9.06 (d, 1H, J=2.3 Hz), 9.02 (d, 1H, J=1.7 Hz), 8.91 (d, 1H, J=1.7 Hz), 8.24 (d, 1H, J=2.3 Hz), 2.65 (s, 3H). |