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Current Organic Synthesis

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ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

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Review Article

Recent Advancements in the Synthesis of α-fluoroalkylated Azine-derived Heterocycles through Direct Fluorination

Author(s): Oksana M. Shavrina, Yuliya V. Rassukana and Petro P. Onysko*

Volume 21, Issue 8, 2024

Published on: 02 November, 2023

Page: [1053 - 1074] Pages: 22

DOI: 10.2174/0115701794271650231016094853

Price: $65

Abstract

The review highlights recent advancements in the synthesis of α-fluoro and α,α- difluoroalkylated azines, focusing on two main approaches. The first approach involves nucleophilic deoxofluorination, wherein α-hydroxy- or α-oxoalkylated azines are treated with diethylaminosulfur trifluoride or other S-F reagents to introduce fluorine atoms. The second approach employs direct electrophilic benzylic fluorination, whereby alkylazines undergo fluorination using N-F reagents. Both methods provide flexibility in designing and synthesizing fluoroalkylated heterocycles.

Keywords: Alkylazines, pyridines, pyrimidines, fluorination, fluoromethyl, difluoromethyl, N-F fluorinating agents, diethylaminosulfur trifluoride.

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