Work

Mechanistic and Kinetic Studies of Reductions of α,β Unsaturated Esters and Ketones by SmI 2 –Water

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide The coupling of ketones with activated olefins is an important class of reactions that has been widely proposed to undergo initial reduction of the ketone, followed by radical addition of the intermediate ketyl to the olefin. In an initial study, we examined the rate of reduction of several α,β unsaturated esters and cyclic ketones by SmI 2 –water. These studies demonstrate that the rate of reduction of the activated olefin is substantially faster than that of the ketones examined. We also uncovered an unusual rate order dependence for water in the reduction of α,β unsaturated esters.

Source: Organic Letters

DOI: 10.1021/acs.orglett.5c04408

Authors: Jonathan B. Hixson-Cooper, Robert A. Flowers

Institution: Lehigh University

Language: English

Topic: Organometallic Complex Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funder: Division of Chemistry