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The TEMPO/Copper Catalyzed Oxidation of Primary Alcohols to Aldehydes Using Oxygen as Stoichiometric Oxidant

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Summary.

A catalytic system for the selective oxidation of primary alcohols to aldehydes under very mild conditions was developed. The catalytic system is based on TEMPO and Cu(II), which is generated in situ by oxidation of elemental copper and chelated by means of 2,2′-bipyridine. Compared to existing Cu/TEMPO oxidation methods we substantially lowered the amount of copper necessary and discovered that the reaction is dependent on pH. The catalytic system was also tested with polymer-bound TEMPO and new insights into the currently discussed mechanism were derived.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Johannes Kepler University Linz, A-4040, Linz, Austria

    David Geißlmeir & Heinz Falk

  2. DSM Fine Chemicals Austria, Research and Development, A-4021, Linz, Austria

    Walther G. Jary

Authors
  1. David Geißlmeir
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  2. Walther G. Jary
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  3. Heinz Falk
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Correspondence to Heinz Falk.

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Geißlmeir, D., Jary, W. & Falk, H. The TEMPO/Copper Catalyzed Oxidation of Primary Alcohols to Aldehydes Using Oxygen as Stoichiometric Oxidant. Monatsh. Chem. 136, 1591–1599 (2005). https://doi.org/10.1007/s00706-005-0349-0

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  • DOI: https://doi.org/10.1007/s00706-005-0349-0

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