Toward Ideal (Trans)Esterification by Use of Fluorous Distannoxane Catalysts

• Published in: Accounts of chemical research Vol. 37; no. 5; pp. 288 - 296
• Main Author: Otera, Junzo
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 01-05-2004
• ISSN: 0001-4842; 1520-4898
• DOI: 10.1021/ar030146d

1,3-Disubstituted tetrakis(fluoroalkyl)distannoxanes, (XR2SnOSnR2Y)2 (R = C6F13C2H4 and C4F9C2H4), 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.