- Nickel-catalyzed reductive monofluoroakylation of alkyl tosylate with bromofluoromethane to primary alkyl fluoride
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A nickel-catalysed direct terminal monofluoromethlyation between alkyl tosylates and a low-cost, industrial raw material bromofluoromethane has been developed. This transformation has demonstrated high efficiency, mild conditions, and good functional-grou
- Cui, Ru,Hu, Duo-Duo,Sheng, Jie,Wang, Xi-Sheng,Wu, Bing-Bing,Zheng, Hong-Qian
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supporting information
p. 9084 - 9087
(2021/09/14)
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- Diversity-Oriented Synthesis of Aliphatic Fluorides via Reductive C(sp3)?C(sp3) Cross-Coupling Fluoroalkylation
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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.
- Sheng, Jie,Ni, Hui-Qi,Ni, Shan-Xiu,He, Yan,Cui, Ru,Liao, Guang-Xu,Bian, Kang-Jie,Wu, Bing-Bing,Wang, Xi-Sheng
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supporting information
p. 15020 - 15027
(2021/06/11)
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