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. 2022 Aug 29:18:1116-1122.
doi: 10.3762/bjoc.18.114. eCollection 2022.

Electrogenerated base-promoted cyclopropanation using alkyl 2-chloroacetates

Kouichi Matsumoto  1 , Yuta Hayashi  1 , Kengo Hamasaki  1 , Mizuki Matsuse  1 , Hiyono Suzuki  1 , Keiji Nishiwaki  2 , Norihito Kawashita  3
Affiliations

Electrogenerated base-promoted cyclopropanation using alkyl 2-chloroacetates

Kouichi Matsumoto et al. Beilstein J Org Chem. .

Abstract

The electrochemical reduction conditions of the reaction of alkyl 2-chloroacetates in Bu4NBr/DMF using a divided cell equipped with Pt electrodes to produce the corresponding cyclopropane derivatives in moderate yields were discovered. The reaction conditions were optimized, the scope and limitations, as well as scale-up reactions were investigated. The presented method for the electrochemical production of cyclopropane derivatives is an environmentally friendly and easy to perform synthetic procedure.

Keywords: alkyl 2-chloroacetates; cyclopropane derivatives; divided cell; electro-reduction.

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Figures

Scheme 1
Scheme 1
Formations of 1,2,3-trialkyl cyclopropanetricarboxylates. Previous reports (reactions 1–3) and this work (reaction 4).
Scheme 2
Scheme 2
Plausible reaction mechanism. EGB = electrogenerated base.
See this image and copyright information in PMC

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