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Current Organic Synthesis

Author(s): Tegene T. Tole*, Johannes H.L. Jordaan and Hermanus C.M. Vosloo

DOI: 10.2174/1570179417666200212111049

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α-Pyridinyl Alcohols, α,α’-Pyridine Diols, α-Bipyridinyl Alcohols, and α,α’-Bipyridine Diols as Structure Motifs Towards Important Organic Molecules and Transition Metal Complexes

Page: [344 - 366] Pages: 23

  • * (Excluding Mailing and Handling)

Abstract

Background: The preparation and use of pyridinyl alcohols as ligands showed incredible increment in the past three decades. Important property of pyridinyl alcoholato ligands is their strong basicity, which is mainly due to the lack of resonance stabilization of the corresponding anion. This strongly basic anionic nature gives them high ability to make bridges between metal centers rather than to bind to only one metal center in a terminal fashion. They are needed as ligands due to their ability to interact with transition metals both covalently (with oxygen) and hemilabile coordination (through nitrogen).

Objective: The review focuses on the wide application of α-pyridinyl alcohols, α,α’-pyridine diols, α- bipyridinyl alcohols, and α,α’-bipyridine diols as structure motifs in the preparation of important organic molecules which is due to their strongly basic anionic nature.

Conclusion: It is clear from the review that in addition to their synthetic utility in the homogeneous and asymmetric catalytic reactions, the preparation of the crown ethers, cyclic and acyclic ethers, coordinated borates (boronic esters), pyridinyl-phosphine ligands, pyridinyl-phosphite ligands, and pyridinyl-phosphinite ligands is the other broad area of application of pyridinyl alcohols. In addition to the aforementioned applications they are used for modeling mode of action of enzymes and some therapeutic agents. Their strongly basic anionic nature gives them high ability to make bridges between metal centers rather than to bind to only one metal center in a terminal fashion in the synthesis of transition metal cluster complexes. Not least numbers of single molecule magnets that can be used as storage of high density information were the result of transition metal complexes of pyridinyl alcoholato ligands.

Keywords: Complex, crown ether, pyridinyl-phosphine ligand, pyridinyl-phosphite ligand, pyridinyl-phosphinite ligand, polyether, preparation.

Graphical Abstract

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