Issue 18, 2022

Cu catalyzed [4 + 2] cycloaddition for the synthesis of highly substituted 3-fluoropyridines

Abstract

A copper catalyzed annulation–aromatization of benzyl trifluoromethyl ketimines with 3-acryloyloxazolidin-2-ones for the synthesis of 3-fluoropyridines through double C–F bond cleavages has been developed. In this approach, the annulation occurred between the in situ formed dienes from trifluoromethyl ketimines via the first C-F bond cleavage and 3-acryloyloxazolidin-2-ones. Then the aromatization afforded 3-fluoropyridines in moderate yields through the second C–F bond cleavage. The 3-fluoropyridine products could be further hydrolyzed to multi-substituted 3-pyridinecarboxylic acids.

Graphical abstract: Cu catalyzed [4 + 2] cycloaddition for the synthesis of highly substituted 3-fluoropyridines

Supplementary files

Article information

Article type
Communication
Submitted
21 Jan 2022
Accepted
14 Apr 2022
First published
18 Apr 2022

Org. Biomol. Chem., 2022,20, 3731-3736

Cu catalyzed [4 + 2] cycloaddition for the synthesis of highly substituted 3-fluoropyridines

Y. Fu, H. Shi, S. Lei, L. Shi and H. Li, Org. Biomol. Chem., 2022, 20, 3731 DOI: 10.1039/D2OB00133K

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