Electrochemical Synthesis of 2-Bromoethyl and 2-Iodoethyl Ketones from Cyclopropanols

Abstract

A simple electrochemical protocol for the preparation of 2-bromoethyl- and 2-iodoethyl ketones from cyclopropanols and magnesium halides has been developed. The reaction proceeded with exclusive regioselectivity and without epimerization of the α-stereocenter in the products. We also showed that the synthesized diastereomerically pure 2-bromoethyl ketones undergo smooth copper and nickel-catalyzed alkylation, alkenylation, and arylations reactions.

Key words

electrochemistry - cyclopropanols - haloethyl ketones - ring opening - cross-coupling

Publication History

Received: 27 July 2021

Accepted after revision: 21 September 2021

Accepted Manuscript online:
21 September 2021

Article published online:
08 October 2021

• References and Notes


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