Toward Ideal (Trans)Esterification by Use of Fluorous Distannoxane Catalysts
- 12 February 2004
- journal article
- Published by American Chemical Society (ACS) in Accounts of Chemical Research
- Vol. 37 (5), 288-296
- https://doi.org/10.1021/ar030146d
Abstract
1,3-Disubstituted tetrakis(fluoroalkyl)distannoxanes, (XR(2)SnOSnR(2)Y)(2) (R = C(6)F(13)C(2)H(4) and C(4)F(9)C(2)H(4)), are highly fluorophilic and exhibit large partition coefficients in favor of fluorocarbon solvents over common organic solvents due to a double-layered structure where the stannoxane core is covered by fluoroalkyl groups. Under catalysis of these Lewis acids, fluorous technology allows novel transesterification and esterification in which a 100% yield of the desired esters is achievable with reactants in a strict 1:1 ratio. The catalysts are recovered from the fluorous phase quantitatively. More practically, the catalyst in fluorocarbon solution can be recycled for use in the next reaction repeatedly.Keywords
This publication has 20 references indexed in Scilit:
- EsterificationPublished by Wiley ,2003
- Direct ester condensation from a 1:1 mixture of carboxylic acids and alcohols catalyzed by hafnium(IV) or zirconium(IV) saltsTetrahedron, 2002
- Recent Advances in High-Resolution Solid-State NMR SpectroscopyAngewandte Chemie-International Edition, 2001
- Direct Condensation of Carboxylic Acids with Alcohols Catalyzed by Hafnium(IV) SaltsScience, 2000
- Fluorous Biphase ChemistryAccounts of Chemical Research, 1998
- Are Teflon "Ponytails" the Coming Fashion for Catalysts?Science, 1994
- TransesterificationChemical Reviews, 1993
- The Atom Economy—A Search for Synthetic EfficiencyScience, 1991
- Novel template effects of distannoxane catalysts in highly efficient transesterification and esterificationThe Journal of Organic Chemistry, 1991
- Hydrozirconation. Organic synthesis via organozirconium intermediates. Synthesis and rearrangement of alkylzirconium(IV) complexes and their reaction with electrophilesJournal of the American Chemical Society, 1974