Publication: Pd(II)-catalyzed deprotection of acetals and ketals containing acid sensitive functional groups
Authors
Juliá Hernández, Francisco ; Arcas, Aurelia ; Vicente, José
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Publisher
Elsevier
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DOI
https://doi.org/10.1016/j.tetlet.2013.12.067
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info:eu-repo/semantics/article
Description
© 2014. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/.This document is the Accepted version of a Published Work that appeared in final form in Tetrahedron Letters. To access the final edited and published work see https://doi.org/10.1016/j.tetlet.2013.12.067
Abstract
The pincer complex [Pd(C1,O1,N1-L)(NCMe)]ClO4 (L = monoanionic ligand resulting from deprotonation of the acetyl group of the dimethyl monoketal of 2,6-diacetylpyridine) is used for the high-yield and selective catalytic hydrolysis of aliphatic, aromatic, cyclic and acyclic dimethyl-acetals, -
ketals and dioxolanes, even in the presence of large substituents. Other protecting groups, as THP or TBDMS, or very acid-sensitive alcohols were not affected. The catalyst is easily prepared in high yield from Pd(AcO)2 and 2,6-diacetylpyridinium perchlorate stable to air and moisture, easily and fully
recoverable and reusable.
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Citation
Tetrahedron Letters 2014, 55, 1141-1144
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