Scale-Up Guide: Suzuki-Miyaura Cross-Coupling Reaction

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Important Note

All of the preformed catalysts used in the kit are air and moisture stable complexes in their commercially available form. Once activated by base under the reaction conditions they become sensitive to air. To best enable scale-up success, the use of standard Schlenk technique is recommended.

General Guidelines for Catalytic Reaction Scale-Up

  • Oven dry all glassware and stir bars
  • Preheat oil bath to avoid temperature spiking
  • Use dry, high purity reagents (and substrates)1
  • Use unopened Sure/Seal™ anhydrous solvents (or newly degassed)1
  • Keep reactions under an atmosphere of nitrogen
  • Purge needle/syringe with nitrogen prior to use

Example Experimental

All solids (substrates/catalyst) were weighed on a bench top balance and added to a cooled, oven dried flask1,2 equipped with an oven dried stir bar. The reaction was capped and then purged and backfilled with nitrogen (3x) with a nitrogen-fed manifold needle. Anhydrous solvent (SureSeal™ed and punctured with a nitrogen-fed manifold needle) was then added via syringe. The aq. base was first degassed and then it was added as the final component via syringe. When all constituents were added, the nitrogen line was removed3 and the reaction allowed to stir at the required temperature for the duration of the reaction.

  1. See the Cross-Coupling Reaction Manual: Desk Reference and Cross-Coupling Quick Guide: Bench Reference for more detailed additional guidance and troubleshooting tips
  2. Reaction vials capable of being sealed with a microwave cap are very useful as well. By design, the caps do not need to be replaced once punctured.
  3. For higher temps, a reflux condenser operated under nitrogen can be used.

Suzuki-Miyaura Cross-Coupling Reaction Product List

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Description Product No.   Vial
XPhos-Pd-G3 763381
A1, B1, C1, D1
SPhos-Pd-G2 753009 A2, B2, C2, D2
cataCXium® A Pd G3 761435 A3, B3, C3, D3
APhos-Pd-G3 764183 A4, B4, C4, D4
P(Cy3)-Pd-G3 764175 A5, B5, C5, D5
PEPPSI -IPENT 732117 A6, B6, C6, D6

Other materials to be noted:

   Description    Product No.
Toluene 244511
DMAc 271012
THF 401757
Butanol 281549

Materials

     
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