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

Chen，Shu Jie1; Li，Jia Hui1; He，Zhi Qing1; Chen，Guo Shu1; Zhuang，Yin Yin1; Chen，Chang Ping1; Liu，Yun Lin1,2,3

2022-11-18

10.1021/acs.joc.2c02323

JOURNAL OF ORGANIC CHEMISTRY   Impact Factor & Quartile

0022-3263

1520-6904

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.

SCI

English

Others

WOS:000882962300001

CHEMISTRY

2-s2.0-85141997033

Scopus

1.School of Chemistry and Chemical Engineering,Guangzhou University,Guangzhou,510006,China
2.State Key Laboratory of Functions and Applications of Medicinal Plants,Guizhou Medical University,Guiyang,550014,China
3.Guangdong Provincial Key Laboratory of Catalysis,Southern University of Science and Technology,Shenzhen,518055,China

Chen，Shu Jie,Li，Jia Hui,He，Zhi Qing,et al. N-Trifluoropropylation of Azoles through N-Vinylation and Sequential Hydrogenation[J]. JOURNAL OF ORGANIC CHEMISTRY,2022,87(22):15703-15712.

Chen，Shu Jie.,Li，Jia Hui.,He，Zhi Qing.,Chen，Guo Shu.,Zhuang，Yin Yin.,...&Liu，Yun Lin.(2022).N-Trifluoropropylation of Azoles through N-Vinylation and Sequential Hydrogenation.JOURNAL OF ORGANIC CHEMISTRY,87(22),15703-15712.

Chen，Shu Jie,et al."N-Trifluoropropylation of Azoles through N-Vinylation and Sequential Hydrogenation".JOURNAL OF ORGANIC CHEMISTRY 87.22(2022):15703-15712.