Synthesis of Quinolizidine-Based 1,4-Azaphosphinines via Cyclization of Heteroarylmethyl(alkynyl)phosphinates
Martin Kos, Tomáš Beránek, Jaroslav Žádný, Natálie Kochová, Karolína Václavíková, Illia Panov, Jan Storch, Ivana Císařová, Jan Sýkora, Vladimír Církva
TL;DR
This paper introduces a new method to create phosphorus-based six-membered rings using a silver-catalyzed reaction, producing novel structures with potential for functional chemistry.
Contribution
A silver-catalyzed cyclization method for synthesizing previously unreported quinolizidine-based 1,4-azaphosphinine scaffolds.
Findings
The silver-catalyzed cyclization achieves full conversion across over 30 derivatives under mild conditions.
The method enables the dearomatization of pyridine to form new quinolizidine-based 1,4-azaphosphinine structures.
The approach expands the structural diversity of phosphorus-containing heterocycles.
Abstract
Intramolecular hydroarylation of (phenylethynyl)phosphinates represents a powerful strategy for constructing six-membered phosphorus heterocycles. In this study, we report a silver-catalyzed cyclization protocol that enables the efficient synthesis of 1,4-aza-phosphorus heterocycles under mild conditions. The approach demonstrates broad substrate tolerance, affording full conversion across more than 30 derivatives. Dearomatization of pyridine leads to the formation of previously unreported quinolizidine-based 1,4-azaphosphinine scaffolds. These novel phosphorus heterocycles expand the structural diversity of phosphorus-containing frameworks and open new opportunities in the chemistry of functional heterocycles.
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Taxonomy
TopicsOrganophosphorus compounds synthesis · Catalytic Cross-Coupling Reactions · Catalytic C–H Functionalization Methods