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Introduction
Polyoxyethanyl α-tocopheryl sebacate, PTS, is a nonionic amphiphile recently introduced by Professor Bruce Lipshutz of UC-Santa Barbara that is proving to be a versatile "solubilizer" for organic molecules in water.1 Lipophilic substrates and catalysts can efficiently enter the 25 nm micelles formed by PTS in water leading to cross-coupling reactions such as metathesis, Suzuki-Miyaura, and Heck reactions at room temperature. Importantly, there is no need for a co-solvent to enhance solubility of water-insoluble substrates in these reactions.
PTS (n = ca. 13)
698717
One simply places the requisite amount of PTS (15 wt% in water) into a test tube with a stir bar and adds the organic substrate(s) and catalyst. Reactions are generally complete within 3–24 hours and can be accelerated if needed upon mild heating to 40–50 °C. Work-up is also very convenient involving either extraction of the reaction mixture with EtOAc/hexane or deposition onto a bed of silica gel and elution with EtOAc. In most examples, studied PTS outperformed other nonionic amphiphiles such as Triton®-X100 and Brij® 30. The following examples highlight some of the "PTS chemistry" reported by Professor Lipshutz thus far.
Reference
- Sold under license from Zymes, LLC.
Representative Applications
Olefin Cross Metathesis
Reference
Lipshutz, B. H. et al. Org. Lett. 2008, 10, 1325.
Olefin Ring Closing Metathesis
Reference
Lipshutz, B. H. et al. Adv. Synth. Catal. 2008, 350, 953.
Suzuki-Miyaura Coupling
Reference
Lipshutz, B. H. et al. Org. Lett. 2008, 10, 1333.
Sonogashira Coupling
Reference
Lipshutz, B. H. et al. Org. Lett. 2008, 10, 3793.
Heck Coupling
References
- Lipshutz, B. H.; Taft, B. R. Org. Lett. 2008, 10, 1329.
- Both acrylates and styrenes can now be run in ≤ 5% PTS/water in couplings with aryl iodides; see Lipshutz, B. H.; Ghorai, S. Aldrichimica Acta, in press.
Product Information
| Product No. |
Product Name |
Structure |
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| 698717 |
Polyoxyethanyl α-tocopheryl sebacate |
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