Work

Single-Step Synthesis of 1,2-Cyclopentanediones by Dehydrogenative Annulation of Ethylene Glycol with Secondary Alcohols

Year: 2025

Type: article

Abstract: Alcohol coupling reactions that are induced by alcohol dehydrogenation, and generate hydrogen or water as the only byproducts, have become a well-recognized way to carry out important synthetic transformations, such as esterification and alkylation, in a green and atom-economical fashion. Herein, we report a new type of alcohol-alcohol coupling reaction that involves the dehydrogenative annulation of ethylene glycol with secondary alcohols to give 1,2-cyclopentanedione derivatives in a single synthetic step. This process, which is catalyzed by a pincer complex of earth-abundant manganese, represents a new approach for constructing structurally complicated products from inexpensive, readily available alcohols.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.5c14910

Authors: Lijun Lu, Jie Luo, Michael Montag, Yael Diskin-Posner, David Milstein

Institution: Weizmann Institute of Science

Language: English

Topic: Asymmetric Hydrogenation and Catalysis

Subfield: Inorganic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funder: United States-Israel Binational Science Foundation