Chemistry in Water Reproducibility Study: Learnings from a Precompetitive, Multicompany Collaboration DOI
Richard J. Fox, J. Daniel Bailey, Jennifer V. Obligacion

et al.

Organic Process Research & Development, Journal Year: 2024, Volume and Issue: 28(4), P. 978 - 1002

Published: March 15, 2024

Despite the reported successes and advantages involving use of amphiphilic surfactants, most notably TPGS-750-M, to enable a multitude synthetic transformations be conducted in water, implementation this methodology within pharmaceutical industry has been relatively limited. In paper, we will disclose key results learnings from multicompany collaboration focused on reproducibility study some commonly used reaction types industry, specifically amidation, SNAr, nitro reduction, reductive amination, multiple Pd-catalyzed water. The presentation not just originally TPGS-750-M conditions but also under water-only control with three different as well both small (i.e., ≤500 mg) mid (∼10 g) scales.

Language: Английский

Micellar Catalysis as a Tool for C–H Bond Functionalization toward C–C Bond Formation DOI Creative Commons
Elena Borrego, Ana Caballero, Pedro J. Pérez

et al.

Organometallics, Journal Year: 2022, Volume and Issue: 41(22), P. 3084 - 3098

Published: Aug. 15, 2022

Micelles generated upon dissolving surfactants in water can be employed as nanovessels for catalytic transformations, the so-called micellar catalysis methodology. This review is focused on use of context functionalization carbon–hydrogen bonds. The micelles accumulate catalyst and reactants their inner volume such a high local concentration that kinetics are favored. consequence that, most cases, processes conventional organic solvents require temperatures long reaction times achieved milder conditions when employed.

Language: Английский

Citations

31

Cu-catalysed Chan–Lam synthesis of unsymmetrical aryl chalcogenides under aqueous micellar conditions DOI
Nan Sun, Kai Zheng, Mingqiang Zhang

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(7), P. 2782 - 2789

Published: Jan. 1, 2023

Herein, we report a green and sustainable Cu-catalysed Chan–Lam oxidative protocol for the synthesis of (hetero)aryl selenides/sulfides from diorganyl dichalcogenides boronic acids in an aqueous micellar medium.

Language: Английский

Citations

17

Recent advances in water-mediated multiphase catalysis DOI
Lixin Chen, Shihui Zhang,

Xuemin Liu

et al.

Current Opinion in Colloid & Interface Science, Journal Year: 2023, Volume and Issue: 65, P. 101691 - 101691

Published: March 17, 2023

Language: Английский

Citations

17

Influence of Chain Length and Concentration-Dependent Morphological Switching on Oxidation of Aromatic Alcohols in a Micellar Environment DOI
Mousumi Layek,

Priya Karmakar,

Prashanta Pal

et al.

Industrial & Engineering Chemistry Research, Journal Year: 2024, Volume and Issue: 63(3), P. 1334 - 1348

Published: Jan. 8, 2024

Catalytic oxidation of benzyl alcohol (BA), p-chlorobenzyl (p-ClBA) and p-anisyl (p-OMeBA) in aqueous media has been investigated the presence two cationic surfactants, viz. cetylpyridinium chloride (CPCl) dodecylpyridinium (DPCl). The chromium(VI)-governed oxidations such aromatic compounds exhibit an unusual kinetics depending upon concentration CPCl DPCl. Both surfactants catalyzed at lower concentrations while retardation was noticed higher concentrations. catalytic inhibitory functions both sub- postmicellar levels have enlightened based on kinetic CMC (critical micellization concentration). chain length influences profiles processes. Herein, π–π interaction cation−π play important roles solubilization process therefore encourage reaction rate. These strong interactions result a maximum 12-fold enhancement for micellar environment, effect DPCl analyzed dilution effect. morphological alteration aggregates during aids interpretation activity micelles produced by and/or Berezin's model employed to reveal inhibition caused micelles. Morphological from spherical-to-cylindrical shape variable absence substrate supported SAXS (small-angle X-ray scattering), TEM (transmission electron microscopy), FE-SEM (field emission scanning microscopy) analysis.

Language: Английский

Citations

7

Chemistry in Water Reproducibility Study: Learnings from a Precompetitive, Multicompany Collaboration DOI
Richard J. Fox, J. Daniel Bailey, Jennifer V. Obligacion

et al.

Organic Process Research & Development, Journal Year: 2024, Volume and Issue: 28(4), P. 978 - 1002

Published: March 15, 2024

Despite the reported successes and advantages involving use of amphiphilic surfactants, most notably TPGS-750-M, to enable a multitude synthetic transformations be conducted in water, implementation this methodology within pharmaceutical industry has been relatively limited. In paper, we will disclose key results learnings from multicompany collaboration focused on reproducibility study some commonly used reaction types industry, specifically amidation, SNAr, nitro reduction, reductive amination, multiple Pd-catalyzed water. The presentation not just originally TPGS-750-M conditions but also under water-only control with three different as well both small (i.e., ≤500 mg) mid (∼10 g) scales.

Language: Английский

Citations

7