Aryl Compounds of Pentavalent Antimony: Syntheses, Reactions, and Structures

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Compounds of Pentavalent Antimony: Syntheses, Reactions, and Structures V. V. Sharutina, *, A. I. Poddel’skyb, and O. K. Sharutinaa aSouthern

Ural State University (National Research University), Chelyabinsk, Russia Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, Nizhny Novgorod, Russia *e-mail: [email protected]

b

Received March 26, 2020; revised April 27, 2020; accepted May 7, 2020

Abstract—The synthesis methods, some reactions, and specific features of the structures of aryl compounds of pentavalent antimony and examples of their possible use are systematized and described on the basis of an analysis of the works published since 2009 to the present time. Some earlier works are also reviewed due to this special significance. When discussing the synthesis methods, the main attention is given to the most efficient approaches to the syntheses of the aryl compounds, for example, the reactions of ligand redistribution, substitution, and oxidative addition. The formation of heterocyclic antimony compounds is considered. The data on the biological and catalytic activities of selected antimony derivatives are presented. The bibliography consists of 318 references. Keywords: mono-, bi-, and polynuclear antimony(V) compounds, synthesis, oxidative addition reactions, catalytic, bacterial, and anticancer activity DOI: 10.1134/S1070328420100012

Contents Introduction Synthesis of antimony pentaaryl compounds Ar5Sb Antimony derivatives Ar4SbХ and their reactions Synthesis of antimony compounds Ar4SbХ by pentaarylantimony dearylation with acids Synthesis of Ar4SbX compounds from tetraarylantimony halides Synthesis of the pentavalent antimony compounds via the ligand distribution reaction Synthesis of antimony complexes containing tetraarylstibonium cations Synthesis methods and some reactions of antimony derivatives Ar3SbХ2 Synthesis of antimony derivatives from triarylantimony dihalides Oxidation of Ar3Sb derivatives by organic and inorganic oxidants Oxidative method for synthesis of aryl derivatives of antimony(V) from triarylantimony compounds, acid HX, and peroxide Oxidative method for synthesis of organic antimony(V) derivatives from triorganylantimony and ortho-quinones Antimony derivatives Ar2SbХ3 and ArSbХ4 and their reactions Oxidation Substitution Practical use of antimony(V) aryl compounds Conclusions References

INTRODUCTION An increasing interest in organic antimony compounds is mainly determined by a high potential of their application in the very diverse areas of practical activity: as drugs, biocides, fungicides, and reagents and components of catalytic systems during polymerization, in fine organic synthesis, as antioxidants, and others. In the organoantimony derivatives antimony exists in two main oxidation states, +3 and +5, and, correspondingly, forms

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organic compounds of antimony(III) and antimony(V). In many cases, the structures of the antimony(III) derivatives are oligomeric or polymeric, which i