Electrogenerated base-promoted cyclopropanation using alkyl 2-chloroacetates

Kouichi Matsumoto; Yuta Hayashi; Kengo Hamasaki; Mizuki Matsuse; Hiyono Suzuki; Keiji Nishiwaki; Norihito Kawashita

doi:10.3762/bjoc.18.114

Electrogenerated base-promoted cyclopropanation using alkyl 2-chloroacetates

Beilstein J Org Chem. 2022 Aug 29:18:1116-1122. doi: 10.3762/bjoc.18.114. eCollection 2022.

Authors

Kouichi Matsumoto¹, Yuta Hayashi¹, Kengo Hamasaki¹, Mizuki Matsuse¹, Hiyono Suzuki¹, Keiji Nishiwaki², Norihito Kawashita³

Affiliations

¹ Department of Chemistry, School of Science and Engineering, Kindai University 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan.
² Department of Pharmaceutical Sciences, Faculty of Pharmacy, Kindai University 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan.
³ Department of Life Science, School of Science and Engineering, Kindai University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan.

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.

Grants and funding

This work was supported in part by JSPS KAKENHI Grants JP 20K05588 (Grant-in-Aid for Scientific Research (C)). K. M. acknowledges the Tokyo Ohka Foundation for The Promotion of Science and Technology for the financial support. This work was also partially supported by 2021 Kindai University Research Enchancement Grants (KD2106 and KD2104).