4.8 Article

Electrochemical Radical Selenylation/1,2-Carbon Migration and Dowd Beckwith-Type Ring-Expansion Sequences of Alkenylcyclobutanols

Journal

ORGANIC LETTERS
Volume 21, Issue 4, Pages 1021-1025

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b04041

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Funding

  1. Soonchunhyang University
  2. Basic Science Research Program through the National Research Foundation of Korea [NRF-2016R1D1A1B03933723]

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Electrochemical oxidative radical selenylation/ 1,2 -carbon migration and Dowd-Beckwith-type ring-expansion sequences of alkenylcyclobutanols were developed in this study. This approach is environmentally benign and uses shelf-stable diselenides as selenium radical precursors and electrons as oxidizing reagents. The present protocol offers a facile way to prepare beta-selenated cyclic ketone derivatives. Under Dowd-Beckwith-type rearrangement, it can afford the corresponding one-carbon ring-expanded ketones.

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