Graphene-catalyzed transacetalization under acid-free conditions

[Display omitted] •1,2- and 1,3-Diols are readily protected by graphene-catalyzed transacetalization.•This is performed under Brønsted and Lewis acid-free conditions.•The methodology features a simple protocol under solvent-free conditions.•The quasi-stoichiometric acetal-to-diol molar ratio simplif...

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Bibliographic Details
Published in:Tetrahedron letters 2016-10, Vol.57 (41), p.4637-4639
Main Authors: Nongbe, Medy C., Oger, Nicolas, Ekou, Tchirioua, Ekou, Lynda, Yao, Benjamin K., Le Grognec, Erwan, Felpin, François-Xavier
Format: Article
Language:English
Subjects:
Acid-free conditions
Chemical Sciences
Diol
Graphene
Heterogeneous catalysis
Transacetalization
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Summary:[Display omitted] •1,2- and 1,3-Diols are readily protected by graphene-catalyzed transacetalization.•This is performed under Brønsted and Lewis acid-free conditions.•The methodology features a simple protocol under solvent-free conditions.•The quasi-stoichiometric acetal-to-diol molar ratio simplifies the work-up.•The heterogeneous nature of graphene allows an easy removal of the catalyst. 1,2- and 1,3-Diols are readily protected as cyclic acetals and ketals through a graphene-catalyzed transacetalization process. The methodology features an atom economic procedure since quasi-stoichiometric conditions have been developed. Unlike prior systems, the graphene-catalyzed transacetalization is performed under Brønsted and Lewis acid-free conditions and without solvent. Our method has been applied to several volatile compounds that are unsuitable for complex work-up and extensive purification steps. The very unusual catalytic properties of graphene for transacetalization reactions are ascribed to molecular charge transfer between graphene and substrates.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2016.09.022