4.7 Article

Ni and Fe catalyzed cascade radical reactions of oxime esters with diselenides

期刊

ORGANIC CHEMISTRY FRONTIERS
卷 9, 期 13, 页码 3480-3485

出版社

ROYAL SOC CHEMISTRY
DOI: 10.1039/d2qo00586g

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资金

  1. Sichuan Science and Technology Program [2021YFH0161]
  2. National Natural Science Foundation of China [21811530004]
  3. Science and Technology Project of Southwest Petroleum University [2021JBGS07]
  4. Swedish Foundation for International Cooperation in Research and Higher Education STINT [CH2017-7226]

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A method for radical cyclization and ring-opening of oxime esters with diselenides has been developed. Both Ni(0) and Fe(ii) catalysts can be used for the selenylation of olefin-containing and cyclic oxime ester derivatives. Using this method, a variety of functionalized pyrrolines and alkyl nitriles can be synthesized in good yields. Additionally, a mechanism involving iminyl radical and carbon-centered radical intermediates has been proposed.
A radical cyclization and ring-opening of oxime esters with diselenides was developed. Both Ni(0) and Fe(ii) catalysts could be employed for the selenylation of olefin-containing and cyclic oxime ester derivatives. With this method, a variety of functionalized pyrrolines and alkyl nitriles were synthesized in good yields. Moreover, a mechanism involving iminyl radical and carbon-centered radical intermediates was proposed.

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