Three‐Component Reaction of p‐Quinone Monoacetals, Amines and Diarylphosphine Oxides to Afford m‐(Phosphinyl)anilides

Abstract

The three‐component reaction of p‐quinone monoacetals, amines and diarylphosphine oxides is developed to afford m‐(diarylphosphinyl)anilides in moderate to high yields. The reaction may proceed via a process involving phospha‐nucleophilic addition to an iminoquinone acetal intermediate and/or carbonyl‐amine condensation with a phosphinyl enone intermediate.

p-Quinol Ethers and p-Quinone Monoacetals as Arylation and Oxidation Reagents: Tandem N-Arylation and α-Functionalization of Pyrrolidine via Redox-Neutral Three-Component Reaction

“…14 16 For example, Qu et al reported the three-component couplings of pyrrolidin-3-ol and p -benzoquinone monoacetal with vinyl- and arylboronic acids to selectively afford cis -2-substituted 3-pyrrolidinols. 16a Recently, we 14` e f g h and others 16b c reported a series of transformations involving QMAs, primary amines/amino acids, with/without another nucleophile to afford 3-aminoarylphosphoryl products, N -aryl-2-arylpyrrolidines, octahydrodipyrroloquinolines, and bridged oxocyclic compounds selectively. Here, we report our results on two sets of MCRs involving QEs/QMAs as both the arylation components and the oxidants, and H-phosphine oxides/naphthols as the terminating nucleophiles to accomplish the process of N -arylation of the simple pyrrolidine with α-phosphinylation or arylation.…”

Green-inspired synthetic drives for organophosphorus compounds under solvent-free conditions

“…[23][24][25][26][27] Recently, various 'greener' pathways as alternatives to traditional chemical syntheses and transformations have been invented in diverse fields of organic chemistry, including organophosphorus chemistry, to attain greater sustainability through newer concepts. [28][29][30][31][32][33] The practice of 'green' chemistry comprises many aspects. Among them, designing solvent-free techniques is noteworthy.…”

Pyrrolidine‐Catalyzed Annulations of Quinone Monoacetals with Naphthols: Synthesis of 2‐Oxabicyclo[3.3.1]nonane Skeletons, Transformations and Reaction Mechanism

“…With a recent interest in developing new synthetic methods for nitrogen‐ and phosphorus‐functionalized aromatics by the use of QMAs as arylation reagents, we have reported the three‐component reactions involving QMAs, amines or α‐amino acids with the third trapping reagents [16] . The reactions, presumably involving selective generation of iminoquinone acetal intermediates from the ketone‐amine condensation of QMAs, provide a platform to access a diversity of functionalized products via selective interceptions of the intermediates [16d–g,17] . These findings invoke our interest in exploring catalytic annulations of QMAs for the synthesis of bridged ring systems.…”