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Synlett 2025; 36(13): 1927-1931
DOI: 10.1055/a-2604-4702
DOI: 10.1055/a-2604-4702
letter
Oxone-Mediated Mild Removal of an Azine Protecting/Directing Group for Applications in Organic Synthesis
Abstract
Azine derivatives of carbonyl compounds are used as protecting groups and have recently been utilized as directing groups in C–H activation. The stability of the azine functional group limits its application in areas where its subsequent removal is desirable. We herein report a mild and efficient method for removal of an azine group using Oxone as a green oxidant in the presence of an acetone/water solvent system. Carbonyl regeneration occurs in high yields from a range of aldazine and ketazine derivatives. A gram-scale synthesis and removal of the azine directing group from an ortho-functionalized azine are performed to extend the application of this methodology.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2604-4702.
- Supporting Information
Publication History
Received: 02 February 2025
Accepted after revision: 08 May 2025
Accepted Manuscript online:
08 May 2025
Article published online:
03 July 2025
© 2025. Thieme. All rights reserved
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