Work

A Broadly Applicable Strategy to Aminate Azines Enabled by Electronically Tuned Phosphine Reagents

Year: 2025

Type: article

Abstract: We describe a strategy for aminating pyridines and other azines via phosphonium salt intermediates. Precisely tuning the electronic properties of the phosphonium ion was key for C─N bond formation via an S N Ar‐halogenation, S N Ar‐amination sequence. The process couples a wide range of amine classes with pyridines and is viable for applications such as late‐stage amination of complex pharmaceuticals and fragment–fragment coupling reactions. The capacity to rapidly modify the structure of the phosphine reagent was decisive and is a valuable feature in pseudohalide design.

Source: Angewandte Chemie

DOI: 10.1002/ange.202512024

Authors: Ren‐Rong Liu, Jeffrey N. Levy, Andrew McNally

Institution: Colorado State University

Language: English

Topic: Organophosphorus compounds synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Institutes of Health, National Institute of General Medical Sciences

Awards: G4470799747, G9000144455, Selective Methods to Transform Pyridines and Diazines that Facilitate Medicinal Chemistry