N-Trifluoropropylation of Azoles through N-Vinylation and Sequential Hydrogenation.

Installing a fluoroalkyl group onto the nitrogen atom of azoles represents a potential strategy for lead optimization in medicinal chemistry. Herein, we describe a method for the N-trifluoropropylation of azoles. This process is accomplished using a combination of regioselective N-vinylation and sequential hydrogenation. The two-step sequence is applicable to a diverse set of azoles and tolerates a wide range of functionalities. In addition, we showcase its practicability and utility through the gram-scale synthesis and the late-stage modification of a complex molecule.

Citation

Shu-Jie Chen, Jia-Hui Li, Zhi-Qing He, Guo-Shu Chen, Yin-Yin Zhuang, Chang-Ping Chen, Yun-Lin Liu. N-Trifluoropropylation of Azoles through N-Vinylation and Sequential Hydrogenation. The Journal of organic chemistry. 2022 Nov 18;87(22):15703-15712

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PMID: 36331418

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