Issue 7, 2023

Synthesis of fluorinated allylic alcohols via photoinduced decarboxylative cross-coupling of α-fluoroacrylic acids and alcohols

Abstract

Herein, a practical and robust methodology for photoinduced decarboxylative and dehydrogenative cross-coupling is reported. A wide range of α-fluoroacrylic acids and structurally diverse alcohols were smoothly converted into the desired fluorinated allylic alcohols with high Z-stereoselectivity under mild conditions. These fluorinated allylic alcohols are versatile building blocks and important structural fragments in organic chemistry and pharmaceutical science. The feasibility of this synthetic strategy was fully demonstrated via a gram-scale reaction, further transformations, and late-stage modifications of bioactive molecules.

Graphical abstract: Synthesis of fluorinated allylic alcohols via photoinduced decarboxylative cross-coupling of α-fluoroacrylic acids and alcohols

Supplementary files

Article information

Article type
Research Article
Submitted
15 Jan 2023
Accepted
26 Feb 2023
First published
28 Feb 2023

Org. Chem. Front., 2023,10, 1788-1795

Synthesis of fluorinated allylic alcohols via photoinduced decarboxylative cross-coupling of α-fluoroacrylic acids and alcohols

X. Lu, M. Gao, L. Yu, H. Pan, X. Zhang, R. Huang, K. Yang, F. Shui, Y. Song and G. Yang, Org. Chem. Front., 2023, 10, 1788 DOI: 10.1039/D3QO00068K

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