Miyaura Borylation in a Box

Product No. 802352

Reagents

Compound Catalog No. Equivalents MW Density Amount mmol
Kit Components            
Pd[P(t-Bu)3]2 676578 0.036 511.05   9.2 mg 0.018
B2pin2 473294 1.1 253.94   140 mg 0.55
Potassium acetate 236497 3.0 98.14   148 mg 1.5
TPGS-750-M 733857     1.002 2.0 mL  
User Supplied            
Aryl bromide [ArBr]   1.0       0.5

Precautions

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

Procedure

  1. Add the aryl bromide (0.5 mmol) into the provided 5-mL reaction vial containing a stir bar and preloaded catalyst Pd[P(t-Bu)3]2 (9.2 mg, 0.018 mmol), B2pin2 (140 mg, 0.55 mmol) and KOAc (148 mg, 1.50 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 (2.0 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 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.

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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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