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Free three-dimensional carborane carbanions.

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]₂ ^2-, which is the first example of a discrete molecular dicarbanion. These reactive carbanions are key intermediates in carbon vertex chemistry of carborane clusters.

SUBMITTER: Jayaweera HDAC

PROVIDER: S-EPMC8356735 | biostudies-literature | 2021 Aug

REPOSITORIES: biostudies-literature

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Free three-dimensional carborane carbanions.

Jayaweera H D A Chathumal HDAC Rahman Md Mamdudur MM Pellechia Perry J PJ Smith Mark D MD Peryshkov Dmitry V DV

Chemical science 20210630 31

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 wit ...[more]

PMID: 34447536

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