Issue 31, 2021

Free three-dimensional carborane carbanions


Carbon atom functionalization via generation of carbanions is the cornerstone of carborane chemistry. In this work, we report the synthesis and structural characterization of free ortho-carboranyl [C2B10H11], a three-dimensional inorganic analog of the elusive phenyl anion that features a “naked” carbanion center. The first example of a stable, discrete C(H)-deprotonated carborane anion was isolated as a completely separated ion pair with a crown ether-encapsulated potassium cation. An analogous approach led to the isolation and structural characterization of a doubly deprotonated 1,1′-bis(o-carborane) anion [C2B10H10]22−, which is the first example of a discrete molecular dicarbanion. These reactive carbanions are key intermediates in carbon vertex chemistry of carborane clusters.

Graphical abstract: Free three-dimensional carborane carbanions

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Article information

Article type
Edge Article
22 Apr 2021
27 Jun 2021
First published
30 Jun 2021
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2021,12, 10441-10447

Free three-dimensional carborane carbanions

H. D. A. C. Jayaweera, Md. M. Rahman, P. J. Pellechia, M. D. Smith and D. V. Peryshkov, Chem. Sci., 2021, 12, 10441 DOI: 10.1039/D1SC02252K

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