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Buchwald-Hartwig Amination in a Box

Product No. 802298

Reagents

Compound Catalog No. Equivalents MW Density Amount mmol
Kit Components            
[(π-allyl)PdCl]2 222380 0.016 365.89   3.2 mg 0.008
cBRIDP 693383 0.07 352.49   12.4 mg 0.035
Potassium t-butoxide 156671 1.64 112.21   92 mg 0.82
TPGS-750-M 733857     1.002 1.0 mL  
             
User Supplied            
Aryl bromide [ArBr]   1.0       0.5
Amine [RNH2]   1.2       0.6

Precautions

Please consult the Safety Data Sheet for information regarding hazards and safe handling practices.

Procedure

  1. Add the aryl bromide (0.5 mmol) and the amine (0.6 mmol) into the provided 5-mL reaction vial containing a stir bar and preloaded catalyst [(π-allyl)PdCl]2 (3.2 mg, 0.008 mmol), ligand cBRIDP (12.4 mg, 0.035 mmol) and KO-t-Bu (92 mg, 0.82 mmol) under N2.
  2. Replace the solid top cap with the provided septum top cap and connect with N2 bubbler through a needle.
  3. Transfer the provided TPGS-750-M/H2O (1.0 mL; 2 wt %) solution into the reaction vial using the provided syringe.
  4. Turn on the stirrer and stir the resulting mixture vigorously at room temperature until the reaction is complete (monitored by TLC, GC, LC, etc.).
  5. After completion, dilute the reaction mixture with 1-3 mL of EtOAc (or i-PrOAc) followed by gently stir for 2 minutes and then filter the entire mixture through a bed of silica gel plug (1 inch) on a sintered glass Buchner funnel (30 mm diameter).
  6. Wash the silica gel bed with an additional 1 mL of EtOAc (or i-PrOAc) and collect all of the coupled material.
  7. Remove all of the volatiles in vacuo and purify the crude material by flash column chromatography on silica gel.

More information on the research from the Lipshutz Group can be found in the Professor Product Portal.  

Additional information on TPGS-750-M: Second Generation Amphiphile for Organometallic Chemistry in Water at Room Temperature can be found in the Technology Spotlight section of our website.

Materials

     

 

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