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

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

Research output: Contribution to journalArticlepeer-review

104 Scopus citations

Abstract

A scalable, continuous-flow process has been developed to implement a homogeneous CuI/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% O2 in N2) 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.

Original languageEnglish (US)
Pages (from-to)1247-1251
Number of pages5
JournalOrganic Process Research and Development
Volume17
Issue number10
DOIs
StatePublished - Oct 18 2013
Externally publishedYes

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