Cesium carbonate mediated C-H functionalization of perhalogenated 12-vertex carborane anions

Sergio O Lovera; Alex L Bagsdasarian; Juchen Guo; Hosea M Nelson; Vincent Lavallo

doi:10.1039/d2cc00173j

Cesium carbonate mediated C-H functionalization of perhalogenated 12-vertex carborane anions

Chem Commun (Camb). 2022 Mar 24;58(25):4060-4062. doi: 10.1039/d2cc00173j.

Authors

Sergio O Lovera¹, Alex L Bagsdasarian², Juchen Guo³, Hosea M Nelson², Vincent Lavallo¹

Affiliations

¹ Departments of Chemistry, University of California Riverside, Riverside, CA 92521, USA. [email protected].
² Department of Chemistry and Chemical Engineering, Pasadena, CA 91125, USA. [email protected].
³ Department of Chemical and Environmental Engineering, University of California Riverside, Riverside, CA 92521, USA. [email protected].

PMID: 35262161
DOI: 10.1039/d2cc00173j

Abstract

C-H functionalization of undecahalogenated carborane anions, [HCB₁₁X₁₁^-] (X = Cl, Br, I), is performed with Cs₂CO₃ in acetonitrile. We show that the requisite Cl, Br and I carborane dianions can all be efficiently accessed with Cs₂CO₃. The utilization of Cs₂CO₃ eliminates the complications associated with competing E2 elimination reactions providing an efficient, more functional group tolerant, and broader scope than previously reported. The ensuing functionalized cages provide potential synthons for constructing advanced materials and other molecular architectures for various applications.