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Updated: Jun 18, 2025

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Sacrificial Anode-Free Electrochemical Cross-Electrophile Coupling of 1,3-Diol Derivatives to Form Aliphatic and Aryl
Nadia Hirbawi1, Ethan T A Raffman1, James R Pedroarena1
1Department of Chemistry, University of California, Irvine, California 92697-2025, United States.
Abstract:
Cross-electrophile coupling reactions that forge C(sp3)-C(sp3) bonds are strategic methods for the synthesis of molecules with high F(sp3), yet very few employ electrochemical conditions as the necessary reductant. Herein, we report an electrochemical intramolecular cross-electrophile coupling reaction of 1,3-diol derivatives to access aliphatic and aryl cyclopropanes, including spirocyclic and fused bicyclic cyclopropanes. The scalable electrochemical cross-electrophile coupling (eXEC) reaction employs a nonsacrificial anode in an undivided cell.
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