Continuous-Flow Aerobic Oxidation of Primary Alcohols with a Copper(I)/TEMPO Catalyst

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• 作者：Jodie F. Greene ; Jessica M. Hoover ; David S. Mannel ; Thatcher W. Root ; Shannon S. Stahl
• 刊名：Organic Process Research & Development
• 出版年：2013
• 出版时间：October 18, 2013
• 年：2013
• 卷：17
• 期：10
• 页码：1247-1251
• 全文大小：276K
• 年卷期：v.17,no.10(October 18, 2013)
• ISSN：1520-586X

文摘

A scalable, continuous-flow process has been developed to implement a homogeneous Cu<sup>Isup>/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<sub>2sub> in N<sub>2sub>) 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.