Journal
TETRAHEDRON LETTERS
Volume 56, Issue 21, Pages 2768-2772Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2015.04.033
Keywords
Functional group interconversion; PMB ethers; Carbonyl compounds; Oxidation; Oxygen
Categories
Funding
- National Natural Science Foundation of China [21376224, 21206147]
- Opening Foundation of Zhejiang Key Course of Chemical Engineering and Technology, Zhejiang University of Technology [20130211]
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A facile and efficient protocol for direct transformation of p-methoxybenzyl (PMB) ethers to aldehydes or ketones via a catalytic aerobic oxidation process has been developed. The reaction was performed with the combination of catalytic amounts of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), 2,2,6,6-tetramethylpiperidine N-oxy (TEMPO), and tert-butyl nitrite (TBN), with molecular oxygen as terminal oxidant. A variety of PMB ether substrates derived from benzylic alcohols, heteroaromatic alcohols, and aliphatic alcohols, were converted to their corresponding carbonyl compounds in good conversions and selectivities. (C) 2015 Elsevier Ltd. All rights reserved.
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