Free Three-Dimensional Carborane Carbanions

Author(s)

H.D.A. zzzchathumal Jayaweera
Md. Mamdudur Rahman, University of South CarolinaFollow
Perry J. Pellechia, University of South CarolinaFollow
Mark D. Smith, University of South CarolinaFollow
Dmitry V. Peryshkov, University of South CarolinaFollow

Document Type

Article

Abstract

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.

Digital Object Identifier (DOI)

https://doi.org/10.1039/d1sc02252k

Publication Info

Published in Chemical Science, Volume 12, Issue 31, 2021, pages 10441-10477.

Rights

© The Royal Society of Chemistry 2021

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.

APA Citation

H. D. A. Chathumal Jayaweera, Md. Mamdudur Rahman, Pellechia, P. J., Smith, M. A., & Peryshkov, D. V. (2021). Free three-dimensional carborane carbanions. 12(31), 10441–10447. https://doi.org/10.1039/d1sc02252k