Work

Synthesis of Stereodefined Enones from the Cross-Electrophile Coupling of Activated Acrylic Acids with Alkyl Bromides

Year: 2024

Type: article

Abstract: trisubstituted enones from acrylic acids through the in situ generation of a 2-pyridyl ester and subsequent cross-electrophile coupling with a nickel catalyst under reducing conditions. The scope of trisubstituted enones is broad and compatible with functionality that can be challenging in established olefination techniques. We highlight conditions necessary to suppress undesired side reactions from the α,β-unsaturated carbonyl and improve cross-electrophile coupling approaches to prepare enones.

Source: Organic Letters

DOI: 10.1021/acs.orglett.4c02644

Authors: Omar M. Beleh, Sileen Alomari, Daniel J. Weix

Institution: University of Wisconsin–Madison

Language: English

Topic: Catalytic Cross-Coupling Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Science Foundation, National Institutes of Health, National Institute of General Medical Sciences, Division of Chemistry

Awards: G1711593866, Acquisition of a 400 MHz NMR Spectrometer for Chemical Research and Learning, QExactive (Orbitrap) mass spectrometer, Nickel Cross-Coupling Cascades with α-Heteroatom Radicals to Prepare Sterically Hindered Alcohols and Amines, Cross-Electrophile Coupling for C(sp2)–C(sp3) Bond Formation: Broadened Access to Abundant Electrophiles, Solutions to Challenging Couplings, and Improved Mechanistic Understanding