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. 2024 Aug 9;26(31):6556-6561.
doi: 10.1021/acs.orglett.4c02022. Epub 2024 Jul 31.

Sacrificial Anode-Free Electrochemical Cross-Electrophile Coupling of 1,3-Diol Derivatives to Form Aliphatic and Aryl Cyclopropanes

Nadia Hirbawi  1 , Ethan T A Raffman  1 , James R Pedroarena  1 , Tristan M McGinnis  1 , Elizabeth R Jarvo  1
Affiliations

Sacrificial Anode-Free Electrochemical Cross-Electrophile Coupling of 1,3-Diol Derivatives to Form Aliphatic and Aryl Cyclopropanes

Nadia Hirbawi et al. Org Lett. .

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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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Scheme 1
Scheme 1. C(sp3)–C(sp3) XEC and eXEC Reactions
Scheme 2
Scheme 2. Substrate Scope of the eXEC Reaction
Isolated yields. Reacted at 18 °C for 1 h, then 80 °C for 15 h. Yield determined by 1H NMR based on comparison to PhTMS.
Scheme 3
Scheme 3. Scalability and Sensitivity Screen
See this image and copyright information in PMC

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