Chemical Synthesis

PTS Amphiphile

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. 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.1,2

698717

One simply places the requisite amount of PTS (2–5 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® 30.1,2 The following examples highlight some of the "PTS chemistry" reported by Professor Lipshutz.

Representative Applications

Olefin Cross Metathesis3

Both acrylates and styrenes can now be run in ≤ 5% PTS/water in couplings with aryl iodides.1,2

Sonogashira Coupling4

 

Product Information

Prod. No. Product Name Structure Add to Cart
698717 Polyoxyethanyl α-tocopheryl sebacate