Oxidative cleavage of benzylic and related ethers, using an oxoammonium salt.
Benzylic ethers and related ArCH(2)OR substrates are oxidatively cleaved by 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (1) in wet CH(3)CN 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 carbon as evidenced by slow reaction of substrates bearing electron-withdrawing substituents.
Pradhan
Priya P
PP
Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3060, USA.
Bobbitt
James M
JM
Bailey
William F
WF