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Boxed reaction (Catalog No. 747904): Heck Reaction in Lipshutz Surfactant

Reagents

Compound Catalog No. Equivalents MW Density Amount mmol
Kit Components            
Pd(t-Bu3P)2 676578 0.02 511.05 10 mg 0.02
Triethylamine T0886 3 101.19 0.726 0.42 mL 3.0
TPGS-750-M 763918 (1 M)     2.0 mL  
             
User Supplied            
Aryl iodide [ArI]   1       1.0
alkene   2       2.0

Precautions

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

Procedure

Heck Reaction in Water at Room Temperature using TPGS-750-M (Lipshutz Surfactant)

The catalyst Pd[P(t-Bu)3]2 (10 mg, 0.02 mmol) and aryl iodide (1.0 mmol) are added under argon into a reaction flask containing stir bar. An aliquot of TPGS-750-M/H2O solution (2.0 mL; 5 wt % TPGS-750-M in water), Et3N (0.42 mL, 3.0 mmol), and acrylate/styrene (2.0 mmol) are added sequentially by syringe, and the resulting mixture is allowed to stir at room temperature for 4–12 hours. 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, which is subsequently purified by flash chromatography on silica gel.

Materials

     

 Reference

 

02/14-1

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