Digging the Sigma-Hole of Organoantimony Lewis Acids by Oxidation

Angewandte Chemie
Mengxi YangFrançois P Gabbaï

Abstract

The development of group 15 Lewis acids is an area of active investigation that has led to numerous advances in anion sensing and catalysis. While phosphorus has drawn considerable attention, emerging research shows that organoantimony(III) reagents may also act as potent Lewis acids. Comparison of the properties of SbPh3 , Sb(C6 F5 )3 , and SbArF3 with those of their tetrachlorocatecholate analogues SbPh3 Cat, Sb(C6 F5 )3 Cat, and SbArF3 Cat (Cat=o-O2 C6 Cl4 , ArF =3,5-(CF3 )2 C6 H3 ) demonstrates that the Lewis acidity of electron deficient organoantimony(III) reagents can be readily enhanced by oxidation to the +V state-as verified by binding studies, organic reaction catalysis, and computational studies. The results are rationalized by explaining that oxidation of the antimony center leads to a lowering of the accepting σ* orbital and a deeper carving of the associated σ-hole.

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Citations

Apr 19, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Mengxi YangFrançois P Gabbaï
Jan 3, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Rajesh DekaHarkesh B Singh
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Apr 28, 2021·Journal of the American Chemical Society·Jian ZhangBin Tan
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May 15, 2021·Organic & Biomolecular Chemistry·Di YouFrançois P Gabbaï
Aug 12, 2021·Chemical Communications : Chem Comm·Deepti SharmaAjay Venugopal
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Jul 10, 2019·The Journal of Organic Chemistry·Miao-Miao ZhouLi Dang
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Sep 28, 2021·Angewandte Chemie·Florian S TschernuthShigeyoshi Inoue
Nov 25, 2021·Dalton Transactions : an International Journal of Inorganic Chemistry·Vanessa M GonzalezFrançois P Gabbaï

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