Oxidative cleavage of benzylic and related ethers, using an oxoammonium salt

PP Pradhan, JM Bobbitt, WF Bailey

文献索引：Pradhan, Priya P.; Bobbitt, James M.; Bailey, William F. Journal of Organic Chemistry, 2009 , vol. 74, # 24 p. 9524 - 9527

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被引用次数: 40

摘要

Benzylic ethers and related ArCH2OR substrates are oxidatively cleaved by 4-acetamido-2, 2, 6, 6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (1) in wet CH3CN at room temperature to give the corresponding aromatic aldehyde and alcohol in high yield. Primary or secondary alcohol products are further oxidized by 1 to give carboxylic acids and ketones, respectively. The oxidation likely involves a formal hydride abstraction from the benzylic ...