Electrogenerated base-promoted cyclopropanation using alkyl 2-chloroacetates

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.

Electrochemical Synthesis and Reactivity of Three‐Membered Strained Carbo‐ and Heterocycles

“…A two-electron reduction of phenacyl thiocyanate 76 in an aprotic medium lead to the formation of an enolate 76 a, which can act as a nucleophile as well as an electrogenerated base, resulting in the formation of intermediate Intermediate 78 e coupled with 78 c in a similar manner to yield 78 f. Finally, intramolecular cyclization of 78 f affords the desired product 79 (Scheme 27). [45]…”