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Current Microwave Chemistry

Editor-in-Chief

ISSN (Print): 2213-3356
ISSN (Online): 2213-3364

Research Article

An Easy Deprotection of Tosyl Esters with Superoxide Under Microwave Irradiation

Author(s): Raghvendra S. Raghuvanshi*, Virendra P. Yadav and Vinod K. Singh

Volume 4, Issue 2, 2017

Page: [128 - 130] Pages: 3

DOI: 10.2174/2213335603666161101151340

Price: $65

Abstract

Background: The p-toluenesulfonyl (tosyl) group is one of the most versatile protecting groups for phenols and alcohols, but its removal requires drastic conditions due to their high stability.

Methods: In the course of reaction, (Et4N)O2 was generated in situ by the phase transfer reaction of KO2 and Et4NBr in dry DMF was subsequently allowed to react with tosyl esters, under microwave irradiation.

Results: Tosyl esters were readily deprotected to their corresponding phenols and alcohols.

Conclusion: In conclusion, a mild and efficient method for the removal of tosyl protecting group, using in situ generated tetraethylammonium superoxide under microwave irradiation, has been described.

Keywords: Deprotection, microwave irradiation, superoxide, tosyl esters.

Graphical Abstract

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