Year: 2025
Type: article
Abstract: High Resolution Image Download MS PowerPoint Slide Substituted derivatives of 1,10-phenanthroline are important ligands in inorganic chemistry. Such ligands are often synthesized by nucleophilic addition of aryl- or alkyllithium reagents to the carbon positions adjacent to the phenanthroline nitrogens. The typical reaction sequence (organolithium addition, protonolysis, oxidation, and rearomatization) has been widely used and seldom improved. We sought to replace lithium-based reagents with safer reagents based on magnesium (i.e., Grignards). The effective use of an arylmagnesium reagent in the production of a phenanthroline ligand derivative is now disclosed. Additionally, our newly reported method avoids the use of a heterogeneous oxidant (MnO 2 ) which the traditional method employed in excess. Instead, oxidation due to air exposure is used to achieve the final aromatization step. This new reaction scheme produces 2,9-di( p -methoxyphenyl)-1,10-phenanthroline in a process with a 10.2% average yield.
Source: ACS Omega
Institution: Montclair State University
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: gold
Estimated APC paid: $1,935
Awards: G1034639365, G2516996673, LEAPS-MPS: Topological Control of Ligand Hemilability in Organometallic Nickel Complexes for C-H Activation, G4205161173, Louis Stokes STEM Pathways and Research Alliance: Garden State LSAMP, MRI: Track 1: Acquisition of a Gas Chromatography-Mass Spectrometer for Advancing Research and Education at Montclair State University
OpenAlex ID: W4416673472