4.5 Article

Stepwise radical cation Diels-Alder reaction via multiple pathways

Journal

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 14, Issue -, Pages 704-708

Publisher

BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.14.59

Keywords

Diels-Alder reaction; radical cation; rearrangement; single electron transfer; stepwise

Funding

  1. JSPS KAKENHI Grant [15H04494, 17K19222, 16H06193, 17K19221]
  2. Grants-in-Aid for Scientific Research [16H06193, 17K19222, 15H04494, 17K19221] Funding Source: KAKEN

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Herein we disclose the radical cation Diels-Alder reaction of aryl vinyl ethers by electrocatalysis, which is triggered by an oxidative SET process. The reaction clearly proceeds in a stepwise fashion, which is a rare mechanism in this class. We also found that two distinctive pathways, including direct and indirect, are possible to construct the Diels-Alder adduct.

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