Journal
TETRAHEDRON LETTERS
Volume 56, Issue 21, Pages 2678-2683Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2015.03.120
Keywords
Cleavage of esters; De-protection; Copper-catalyzed; Methanolysis; Sodium azide; Malachite
Categories
Funding
- National Natural Science Foundation of China [21003018]
- Fundamental Research Funds for the Central Universities [N130405005]
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The cleavage of carboxylic acid esters is promoted by malachite in the presence of NaN3 under nearly neutral conditions. In methanol, the aliphatic alcohol esters are converted to methyl esters and corresponding alcohols in good to excellent yields, while the cleavage of phenolic esters gives phenols in quantitative yields. In most cases, the reaction conditions are quite mild so this methodology is efficient for the removal of the acyl-protecting group from the protected hydroxy functional groups. The possible catalytic mechanism is discussed according to some experimental features. (C) 2015 Elsevier Ltd. All rights reserved.
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