Electrocatalytic Activation of Donor-Acceptor Cyclopropanes and Cyclobutanes: An Alternative C(sp )-C(sp ) Cleavage Mode

Overview

Journal Angew Chem Int Ed Engl

Specialty Chemistry

Date 2021 Apr 23

PMID 33890714

Citations 14

Authors

Simon Kolb

Martin Petzold

Felix Brandt

Peter G Jones

Christoph R Jacob

Daniel B Werz

Affiliations

Soon will be listed here.

Abstract

We describe the first electrochemical activation of D-A cyclopropanes and D-A cyclobutanes leading after C(sp )-C(sp ) cleavage to the formation of highly reactive radical cations. This concept is utilized to formally insert molecular oxygen after direct or DDQ-assisted anodic oxidation of the strained carbocycles, delivering β- and γ-hydroxy ketones and 1,2-dioxanes electrocatalytically. Furthermore, insights into the mechanism of the oxidative process, obtained experimentally and by additional quantum-chemical calculations are presented. The synthetic potential of the reaction products is demonstrated by diverse derivatizations.

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