Issue 18, 2022

Four-component defluorinative reaction of allylic fluorides, amidines, and Cs2CO3 under transition-metal-free conditions

Abstract

Research interest in defluorinative functionzalization by means of the distinctive fluorine effect of organofluorides has led to rapid development in this topic. Herein, we reported an unprecedented four-component defluorinative reaction of allylic fluorides, amidines, and Cs2CO3 for the convenient synthesis of valuable pyrimidine-containing amidino carbamates under transition-metal-free conditions. The synthetic linchpin for realizing the multi-bonding tandem protocol relied on the directed function of the α-positioned hydroxyl group and the activating effect of the perfluoroalkyl substituent in allylic fluorides. Moreover, cesium carbonate served as a green carbonyl equivalent for formal CO capture. Mechanistic studies revealed that the reaction proceeded via a possible cyclic carbonate intermediate.

Graphical abstract: Four-component defluorinative reaction of allylic fluorides, amidines, and Cs2CO3 under transition-metal-free conditions

Supplementary files

Article information

Article type
Communication
Submitted
30 May 2022
Accepted
15 Aug 2022
First published
17 Aug 2022

Green Chem., 2022,24, 6816-6822

Four-component defluorinative reaction of allylic fluorides, amidines, and Cs2CO3 under transition-metal-free conditions

Y. Chen, L. Sun, J. Chen, M. Zhu, M. Ma, Z. Shen and X. Chu, Green Chem., 2022, 24, 6816 DOI: 10.1039/D2GC02045A

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