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| SP - THIOPHENOL RESIN, MP |
| PRODUCT: |
| SP–Thiophenol, Resin, MP, a highly cross-linked polystyrene resin functionalized with a Thiophenol end group |
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| APPLICATIONS: |
- SP-Thiophenol resin is a versatile metal-scavenger for palladium, platinum, ruthenium, tin, copper and mercury.
- This metal scavenger is particularly useful for scavenging of residual palladium from palladium-catalyzed hydrogenation and coupling reactions including Suzuki, Buchwald, Stille, Heck, Kumada and Sonogashira.
- SP-Thiophenol resin is equally versatile for the scavenging of a range of alkylating agents including octyl bromide, cinnamyl chloride and benzyl bromide.
- Efficient scavenging of alkyl halides results, in the presence of acid scavengers such as SP-DIEA and SP-Carbonate resin.
- Alternatively, potassium trimethylsilanolate may be used to convert SP-Thiophenol to its thiolate salt for effective scavenging.
- SP-Thiophenol is stable with long-term storage at 40C.
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| PROPERTIES: |
Resin Type: Macroporous poly(styrene-co-divinylbenzene)
Loading: 5.0 – 4.8 mmol/g (based on elemental analysis)
Bead Size: 325-1225 microns, 15-50 mesh (>90% within) |
Typical Palladium
Scavenging Conditions: |
3-5 equiv of the resin relative to palladium content, 8-12 h at ambient temperature |
Typical alkyl halide
Scavenging Conditions: |
2-3 equiv of the resin relative to electrophile at ambient temperature, 1-10 h. Conversion to the thiophenolate with potassium trimethylsilanolate (TMSOK) or use in conjunction with SP-DIEA (2 equiv) and SP-Carbonate (2 equiv) required |
| Compatible Solvents: |
DMF, THF, DCM, MeOH, EtOH, acetonitrile and water |
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| REFERENCES: |
- Kobayashi, S. et al. Tetrahedron Lett, 1996, 37, 5569.
- Barco, A. et al. Tetrahedron Lett, 1998, 39, 7591.
- Roso, V. W. et al. Org Process Res & Dev. 1997, 1, 311.
- Ishihara, K. et al. Chem Lett 2000, 1218.
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