Boxed reaction (Catalog No. 747912): Sonogashira Coupling in Lipshutz Surfactant (TPGS-750-M)

Reagents

Compound Catalog No. Equivalents MW Density Amount mmol
Kit Components            
Pd(CH3CN)2Cl2 225657 0.02 651.75 3 mg 0.02
X-Phos 638064 0.026 476.72 12 mg 0.026
Triethylamine T0886 2 101.19 0.726 0.28 mL 2.0
TPGS-750-M 763918 (1 M)     2.0 mL  
             
User Supplied            
Aryl bromide [ArBr]   1       1.0
alkyne   1.5       1.5

Precautions

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

Procedure

Sonogashira Coupling Reaction in Water at Room Temperature using TPGS-750-M (Lipshutz Surfactant).

The catalyst Pd(CH3CN)2Cl2 (3 mg, 0.01 mmol, Note: this component has been overweighed to account for some residual material left in the vial) and XPhos (12 mg, 0.026 mmol) are added under argon into a reaction flask containing a stir bar. An aliquot of TPGS-750-M/H2O solution (2.0 mL; 2 wt % TPGS-750-M in water), Et3N (0.28 mL, 2.00 mmol), aryl bromide (1.0 mmol), and alkyne (1.5 mmol) are added sequentially by syringe, and the resulting solution is allowed to stir at room temperature for 21–25 hours. The homogeneous reaction mixture is then diluted with EtOAc (2mL), 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, which is subsequently purified by flash chromatography on silica gel.

Materials

     

 Reference

 

02/14-1

Related Links