Work

The organophosphorus synthesis triangle: introducing methods for the missing quaternization and de-quaternization routes

Year: 2025

Type: article

Abstract: PO), into P-stereogenic phosphine oxides and quaternary phosphonium salts. The second transformation is based on the distinctive reactivity of methoxymethyl (MOM)-substituted quaternary phosphonium salts. These compounds undergo a P-C bond cleavage reaction that results in de-quaternization, allowing the synthesis of mixed-substituent tertiary phosphines from triphenylphosphine as a common precursor. Together, these two processes provide multiple efficient synthetic routes to phosphines, phosphine oxides, and quaternary phosphonium salts. The overall synthetic approach is flexible, so that the target compounds can be obtained through several pathways using different substituent combinations as starting materials.

Source: Chemical Science

DOI: 10.1039/d5sc04496k

Authors: Anna C. Vetter, Yannick Ortin, Kirill Nikitin, Declan G. Gilheany

Institution: University College Dublin

Language: English

Topic: Organophosphorus compounds synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

Funders: Synthesis and Solid State Pharmaceutical Centre, Science Foundation Ireland

Awards: G5098725405, G5490111776, G5620247996, Synthesis and Solid State Pharmaceutical Centre (SSPC)