Copper(I)/ABNO-Catalyzed Aerobic Alcohol Oxidation: Alleviating Steric and Electronic Constraints of Cu/TEMPO Catalyst Systems

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• 作者：Janelle E. Steves ; Shannon S. Stahl
• 刊名：Journal of the American Chemical Society
• 出版年：2013
• 出版时间：October 23, 2013
• 年：2013
• 卷：135
• 期：42
• 页码：15742-15745
• 全文大小：359K
• 年卷期：v.135,no.42(October 23, 2013)
• ISSN：1520-5126

文摘

Cu/TEMPO catalyst systems promote efficient aerobic oxidation of sterically unhindered primary alcohols and electronically activated substrates, but they show reduced reactivity with aliphatic and secondary alcohols. Here, we report a catalyst system, consisting of (^MeObpy)Cu^I(OTf) and ABNO (^MeObpy =4,4鈥?dimethoxy-2,2鈥?bipyridine; ABNO = 9-azabicyclo[3.3.1]nonane N-oxyl), that mediates aerobic oxidation of all classes of alcohols, including primary and secondary allylic, benzylic, and aliphatic alcohols with nearly equal efficiency. The catalyst exhibits broad functional group compatibility, and most reactions are complete within 1 h at room temperature using ambient air as the source of oxidant.