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Ruthenium-Catalyzed Oxidative Cleavage of Alkynes to Carboxylic Acids

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Dan Yang,*^†^‡ Fei Chen,^† Ze-Min Dong,^† and Dan-Wei Zhang^‡

Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China, and Department of Chemistry, Fudan University, Shanghai 200433, China yangdan@hku.hk

J. Org. Chem., 2004, 69 (6), pp 2221–2223

DOI: 10.1021/jo0357925

Publication Date (Web): February 26, 2004

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

†

The University of Hong Kong.

‡

Fudan University.

Abstract

We describe an efficient method for the oxidative cleavage of alkynes to carboxylic acids using a combination of RuO₂/Oxone/NaHCO₃ in a CH₃CN/H₂O/EtOAc solvent system. Both internal and terminal alkynes, regardless of their electron density, can be oxidized to carboxylic acids in excellent yield (up to 99%). ¹H NMR spectroscopy and ESI-MS experiments provided evidence for α-diketones and anhydrides as possible intermediates in these oxidation reactions.

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Published In Issue March 19, 2004
Received December 7, 2003

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Ruthenium-Catalyzed Oxidative Cleavage of Alkynes to Carboxylic Acids

Abstract

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Related Content

Ruthenium-Catalyzed Oxidative Cleavage of Olefins to Aldehydes

A greatly improved procedure for ruthenium tetroxide catalyzed oxidations of organic compoundsA greatly improved procedure for ruthenium tetroxide catalyzed oxidations of organic compounds

Copper-Catalyzed Aerobic Oxidative Coupling of Terminal Alkynes with H-Phosphonates Leading to Alkynylphosphonates

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