"TPG-lite": A new, simplified "designer" surfactant for general use in synthesis under micellar catalysis conditions in recyclable water. (7th May 2021)

• Record Type: Journal Article
• Authors: Thakore, Ruchita R.; Takale, Balaram S.; Hu, Yuting; Ramer, Selene; Kostal, Jakub; Gallou, Fabrice; Lipshutz, Bruce H.
• Is Part Of: Tetrahedron. Volume 87(2021)
• Publication Date: 2021-05-07
• Subjects: Micellar catalysis -- Surfactant -- Chemistry in water -- Cross-couplings -- TPG-lite; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2021.132090
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Using the oxidized, carboxylic acid-containing form of MPEG-750, esterification with racemic vitamin E affords a new surfactant (TPG-lite) that functions as an enabling, nanoreactor-forming amphiphile for use in many types of important reactions in synthesis. The presence of a single ester bond is suggestive of simplified treatment as a component of (eventual) reaction waste water, after recycling. Many types of reactions, including aminations, Suzuki-Miyaura, SN Ar, and several others are compared directly with TPGS-750-M, leading to the conclusion that TPG-lite can function as an equivalent nanomicelle-forming surfactant in water. Prima facie evidence amassed via DLS and cryo-TEM analyses support these experimental observations. In silico evaluations of the aquatic toxicity and carcinogenicity of TPG-lite indicate that it is safe to use. Graphical abstract: Image 1