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Boxed reaction: Buchwald-Hartwig in Lipshutz Surfactant

Catalog No. 747599

Reagents

Compound Catalog No. Equivalents MW Density Amount mmol
Kit Components            
[(π-allyl)PdCl]2 222380 0.006 365.89 2 mg 0.006
cBRIDP 693383 0.022 352.49 8 mg 0.022
Potassium t-butoxide 156671 1.6 112.21 180 mg 1.6
TPGS-750-M 733857 (1 M)     1.0 mL  
             
User Supplied            
Aryl bromide [ArBr]   1       1.0
Amine [RNH2]   1.25       1.25

Precautions

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

Procedure

Buchwald-Hartwig Amination Reaction in Water at Room Temperature using TPGS-750-M (Lipshutz Surfactant).

The catalyst [(π-allyl)PdCl]2 (2 mg, 0.006 mmol, Note: this component has been overweighed to account for some residual material left in the vial), ligand cBRIDP (8 mg, 0.022 mmol), KO-t-Bu (180 mg, 1.6 mmol), and amine (1.25 mmol) are sequentially added under argon into a reaction flask containing a stir bar. The TPGS-750-M/H2O (1.0 mL, 2 wt % TPGS-750-M in water) and aryl bromide (1.00 mmol) are added by syringe, and the resulting solution is stirred vigorously at room temperature for 19–20 h. The homogeneous reaction mixture is then diluted with EtOAc (2 mL) and filtered through a bed of silica gel, and the bed is further washed (3 x 5 mL) with EtOAc to collect all of the coupled material. The volatiles are removed in vacuo to afford the crude product that is subsequently purified by flash chromatography on silica gel.

Materials

     

 Reference

  • For more information see Lipshutz, B.H. et al., J. Org. Chem., 76, 4379-4391 (2011) or visit our protocol page

 

11/13-1

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