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Chemical Structure| 787618-22-8 Chemical Structure| 787618-22-8
Chemical Structure| 787618-22-8

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Product Citations

Product Citations

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.

Keywords: Dearomatization ; Hydroamination ; Arenophiles ; Palladium ; Catalysis

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Product Details of RuPhos

CAS No. :787618-22-8
Formula : C30H43O2P
M.W : 466.64
SMILES Code : CC(OC1=C(C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(OC(C)C)=CC=C1)C
MDL No. :MFCD06798294
InChI Key :MXFYYFVVIIWKFE-UHFFFAOYSA-N
Pubchem ID :16217985

Safety of RuPhos

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302+H312+H332-H413
Precautionary Statements:P261-P273-P280-P301+P312

Application In Synthesis of RuPhos

* 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.

  • Downstream synthetic route of [ 787618-22-8 ]

[ 787618-22-8 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 1190363-45-1 ]
  • [ 38573-88-5 ]
  • [ 787618-22-8 ]
  • [ 1190363-46-2 ]
  • C36H46BrF2O2PPd [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate; palladium diacetate; In tert-Amyl alcohol; at 95℃;Inert atmosphere; 4.2.2. Second-generation weak base process. A 10 L reactor equipped with an overhead stirrer was charged with 1 (0.63 kg,1.89 mol), tert-amyl alcohol (2.5 L), potassium phosphate tribasic (1.63 kg,7.56 mol), palladium acetate (10.43 g, 0.046 mol), RuPhos (43.36 g, 0.092 mol), and 2 (0.43 kg, 2.23 mol) under a nitrogen atmosphere. The resulting suspension was heated to 95 °C until 75:25percent v/v as judged by GC analysis. The batch was returned to atmospheric pressure and heated to 40-45 °C. Aq H3PO4 (0.7 L) was slowly added to the mixture while maintaining the batch temperature >40 °C followed by the addition of seeds of 3 (7 g,1 wt percent). The resulting slurry was aged at 40 °C for 1 h. Aq H3PO4 (1.1 L) was slowly added to the batch while maintaining the batch temperature >40 °C . The slurry was held for 1 h at 40 °C , followed by cooling to 0 °C over 6 h. The slurry was isolated by filtration. The wet cake was washed with 47:35:18 percentv/vaq H3PO4/isopropanol/tert-amyl alcohol (12.1 L), 50:50 percentv/v isopropanol/water and dried (50 °C /100 Torr) to provide 3 (0.60 kg,73percent) as an off-white solid.
 

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