1616366-05-2Relevant academic research and scientific papers
Diversity-Oriented Synthesis of Aliphatic Fluorides via Reductive C(sp3)?C(sp3) Cross-Coupling Fluoroalkylation
Sheng, Jie,Ni, Hui-Qi,Ni, Shan-Xiu,He, Yan,Cui, Ru,Liao, Guang-Xu,Bian, Kang-Jie,Wu, Bing-Bing,Wang, Xi-Sheng
supporting information, p. 15020 - 15027 (2021/06/11)
Monofluorinated alkyl compounds are of great importance in pharmaceuticals, agrochemicals and materials. Herein, we describe a direct nickel-catalyzed monofluoromethylation of unactivated alkyl halides using a low-cost industrial raw material, bromofluoromethane, by demonstrating a general and efficient reductive cross-coupling of two alkyl halides. Results with 1-bromo-1-fluoroalkane also demonstrate the viability of monofluoroalkylation, which further established the first example of reductive C(sp3)-C(sp3) cross-coupling fluoroalkylation. These transformations demonstrate high efficiency, mild conditions, and excellent functional-group compatibility, especially for a range of pharmaceuticals and biologically active compounds. Mechanistic studies support a radical pathway. Kinetic studies reveal that the reaction is first-order dependent on catalyst and alkyl bromide whereas the generation of monofluoroalkyl radical is not involved in the rate-determining step. This strategy provides a general and efficient method for the synthesis of aliphatic fluorides.
Efficient synthesis of secondary alkyl fluorides via suzuki cross-coupling reaction of 1-halo-1-fluoroalkanes
Jiang, Xiaojian,Sakthivel, Sekarpandi,Kulbitski, Kseniya,Nisnevich, Gennady,Gandelman, Mark
, p. 9548 - 9551 (2014/07/22)
Organofluorine compounds have found extensive applications in various areas of science. Consequently, the development of new efficient and selective methods for their synthesis is an important goal in organic chemistry. Here, we present the first Suzuki c
