LEWIS ACIDIC PROPERTIES OF ORGANOANTIMONY COMPOUNDS: APPLICATION IN ANION SENSING AND CATALYSIS

In this presentation, we will show that the oxidation of organo-antimony(III) derivatives provides access to Lewis acidic antimony(V) derivatives which can be used in a number of applications ranging from anion sensing to organic reaction catalysis. The first part of the presentation will be dedicated to the chemistry of Lewis basic bidendate distibines and their oxidative conversion into the corresponding distiboranes.^[1] These distiboranes behave as bidendate Lewis acids and readily chelate anions such as the fluoride anion. In the second part of the presentation, we will describe how stibines of general formula R₃Sb can be oxidized even when ligated to transition metal complexes (M). This oxidation induces the formation of a M→Sb interaction which results in a drastic increase in the Lewis acidity of metal center.^[2-4] Using a family of gold stibine derivatives, we will demonstrate that such coordinated stibine oxidation reactions can be used to afford potent hydroamination catalysts.

[1] M. Hirai, F. P. Gabbaï, Angew. Chem. Int. Ed. 2015, 54, 1205-1209.

[2] C. R. Wade, F. P. Gabbaï, Angew. Chem. Int. Ed. 2011, 50, 7369-7372.

[3] H. Yang, T.-P. Lin, F. P. Gabbaı̈, Organometallics 2014, 33, 4368-4373.

[4] J. S. Jones, C. R. Wade, F. P. Gabbaï, Angew. Chem. Int. Ed. 2014, 53, 8876-8879.