4.4 Article

Oxidative umpolung selenocyanation of ketones and arenes: An efficient protocol to the synthesis of selenocyanates

Journal

TETRAHEDRON
Volume 76, Issue 10, Pages -

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2020.130978

Keywords

Selenocyanation; Aryl ketones; Electron-rich arenes; Electrophilic substitution; Umpolung

Funding

  1. National Natural Science Foundation of China [21762008]
  2. Guangxi Natural Science Foundation of China [2018GXNSFAA281245, 2019AC20202]
  3. Bagui Scholar Program of Guangxi Province of China, PR China

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A practical method for the umpolung selenocyanation of aryl ketones, alkyl ketones, beta-ketoesters and electron-rich arenes has been developed, affording various selenocyanates in moderate to excellent yields. This transformation proceeds by an oxidative umpolung selenocyanation through nitrogen oxides-mediated electrophilic selenocyanation process. This method is simpler, more efficient, and less costly than precedent methods. Further transformations of the arylselenocyanate was performed to prove the synthetic utility of this methodology. (C) 2020 Elsevier Ltd. All rights reserved.

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