4.7 Article

Nucleophilic Substitution of Selenosulfonates with Me3SiCF2Br: Facile and Efficient Access to Bromodifluoromethylated Selenides under Metal-Free Conditions

期刊

JOURNAL OF ORGANIC CHEMISTRY
卷 86, 期 24, 页码 18081-18093

出版社

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c02349

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资金

  1. National Natural Science Foundation of China [82172054]
  2. Natural Science Foundation of Jiangsu Province [BK20201133, BK20210062]
  3. Wuxi municipal science and technology development fund [N20192015]
  4. Wuxi Municipal Health Commission Program [Q201946]

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A facile method for synthesizing bromodifluoromethylated selenides under metal-free conditions has been described, with short reaction time, absence of toxic waste, good scalability, and successful late-stage modification of bioactive molecules. The resulting products can be easily converted to different fluorinated and F-18-labeled selenides.
A facile synthesis of bromodifluoromethylated selenides under metal-free conditions is described here. Commercially available Me3SiCF2Br and bench-stable selenosulfonates react smoothly to give a broad scope of alkyl- and aryl-substituted bromodifluoromethylated selenides in moderate to good yields via a difluorocarbene intermediate. This protocol features a short reaction time, the absence of toxic waste, good scalability, and successful late-stage modification of bioactive molecules. In addition, the title products can be easily converted to different fluorinated and F-18-labeled selenides.

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