SABIT™ DVB-TBD
Material overview
SABIT DVB-TBD is a rigid polymeric resin with surface bound superbase TBD (Triazabicyclo[4.4. 0]dec-5-ene) for use in catalytic reactions or as a novel strong anion exchanger. The resin chemistry backbone consists of highly rigid DVB-Styrene with mesopores and a well accessible surface in essentially all solvents. It constitutes a new polymer-bound catalyst with more robust physical properties than other polymer-supported bases.
Table of properties
Property | SABIT DVB-TBD |
Resin backbone | DVB/Sty |
Particle size | 75-200 µm |
Volume of resin, dry | 2.1 ml/g |
Volume of resin, swollen in EtoAc | 2.9 ml/g |
Pore volume | 1 ml/g |
Pore area | 600 m2/g |
Av pore size | 80 Å |
Surface chemistry of SABIT DVB-TBD, with covalently immobilized TBD. Loading ca 1 mmol/g.
Application areas
SABIT DVB-TBD can be used to catalyze a number of reactions, such as Wittig reactions, Michael additions, Henry reactions and transesterifications. Resin-bound TBD is easily separated from substrates and product, facilitating the handling and work-up of product. The resin can be used instead of free TBD or TBD bound to soft resins with only 1-2 % DVB – but these are not compatible with all solvents and do sometimes not perform well. The morphological rigidity and permanent porosity of SABIT DVB-TBD enable its use in a much wider range of solvents and for certain reaction processes it may be the only tool able to catalyze a desired reaction.
Further, this novel resin-bound base can also be employed as a strong anion exchanger and thus as a scavenger for catch and release processes. As described, its unique structure and good water-wettability allow for effective binding in both polar aqueous and non-aqueous solutions.
Activation and regeneration of SABIT DVB-TBD for re-use
Before and after use, polymer-supported TBD resin may be (re-)activated with a strong base (each time ca 5 ml/g resin):
Step | Organic base regeneration | Water-based regeneration |
Strong base wash | 5% MeONa in MeOH | 1 M NaOH, aqu. |
Removal of base | 3 x MeOH | 5 x water |
Removal of organics | Optionally DCM | 3 x MeOH |
Drying | RT or 70 °C oven | RT or 70 °C oven |
Typical application conditions
- Use 2-10 equivalents of catalyst to limiting reactant
- React for 1 – 20 hours while stirring or shaking
- Reaction at room temperature or to max 80 C (possibly higher – to be determined)
- All common solvents are in principle possible to use
- Resin is easily water-wettable and thus also compatible with aqueous mixtures
- After reaction, filter off resin, or let resin sediment, then decant
- Re-activate resin for re-use following suggested regeneration procedure
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