Four-component defluorinative reaction of allylic fluorides, amidines, and Cs₂CO₃ under transition-metal-free conditions
2022
Chen, Yu-Lan | Sun, Li-Wen | Chen, Jia-Wei | Zhu, Ming-Quan | Ma, Mengtao | Shen, Zhi-Liang | Chu, Xue-Qiang
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.
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