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Continuous-flow aerobic oxidation of primary alcohols with a copper(I)/TEMPO catalyst

Organic Process Research and Development, ISSN: 1083-6160, Vol: 17, Issue: 10, Page: 1247-1251
2013
  • 107
    Citations
  • 0
    Usage
  • 97
    Captures
  • 0
    Mentions
  • 0
    Social Media
Metric Options:   Counts1 Year3 Year

Metrics Details

  • Citations
    107
    • Citation Indexes
      107
  • Captures
    97

Article Description

A scalable, continuous-flow process has been developed to implement a homogeneous Cu/TEMPO catalyst system for aerobic oxidation of primary alcohols to aldehydes. This catalyst system is compatible with a wide range of alcohols bearing diverse functional groups. A dilute oxygen source (9% O in N) is used to avoid flammable oxygen/organic mixtures. Residence times in the heated reaction zone can be as low as 5 min with activated (e.g., benzylic) alcohols. The method has been demonstrated with nine different alcohols, including one up to 100 g scale. This flow-based catalytic method exhibits significant advantages for aerobic oxidation of alcohols, including substantially shorter residence times and broader substrate scope relative to a Pd-catalyzed method that we reported recently. © 2013 American Chemical Society.

Bibliographic Details

Jodie F. Greene; Jessica M. Hoover; Shannon S. Stahl; David S. Mannel; Thatcher W. Root

American Chemical Society (ACS)

Chemistry

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