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Palladium-catalyzed oxidation of primary alcohols: Highly selective direct synthesis of acetals

Paper ID Volume ID Publish Year Pages File Format Full-Text
44093 46003 2007 6 PDF Available
Title
Palladium-catalyzed oxidation of primary alcohols: Highly selective direct synthesis of acetals
Abstract

Selective direct synthesis of symmetric acetals through a tandem aerobic oxidation–acetalization of primary alcohols, using a chloride-free Pd(OAc)2/Cu(OAc)2/p-TsOH system as an efficient bifunctional catalyst, has been developed. The reactions occur in neat alcohols with no use of other solvent under mild conditions (50–80 °C, 1–10 atm). p-Toluenesulfonic acid exerts a great accelerative and catalyst stabilizing effect, showing a synergism with Cu(OAc)2. Bimetallic Pd–Cu catalysis is suggested in these reactions. Under similar conditions, a secondary alcohol, propanol-2, reacts more slowly giving mainly acetone. Conventional palladium catalytic systems, such as PdCl2/CuCl2, Pd(OAc)2/LiNO3, and Pd(OAc)2/pyridine, showed no or very low activity in the oxidation of neat n-butanol.

Graphical abstractSelective direct synthesis of acetals through a tandem oxidation–acetalization of primary alcohols, using a chloride-free Pd(OAc)2/Cu(OAc)2/p-TsOH system as an efficient bifunctional catalyst, has been developed. The reaction occurs in neat alcohols with no use of other solvent under mild aerobic conditions. p-Toluenesulfonic acid (p-TsOH) and Cu(OAc)2 exert a great synergetic effect on the reaction rate and selectivity for acetals.Figure optionsDownload full-size imageDownload as PowerPoint slide

Keywords
Palladium; Dioxygen; Oxidation; Primary alcohols; Acetals
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Palladium-catalyzed oxidation of primary alcohols: Highly selective direct synthesis of acetals
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Publisher
Database: Elsevier - ScienceDirect
Journal: Applied Catalysis A: General - Volume 329, 1 October 2007, Pages 1–6
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
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Price was $35.95
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