Direct Synthesis of C-Substituted [RC(O)CH2-CB11H11]− Carborate Anions

A new synthetic method for the synthesis of C-substituted [RC(O)CH2-CB11H11]− carborate anions has been developed. The reaction of [closo-B11H11]2− with terminal alkynes in the presence of a copper catalyst leads to insertion into the boron cluster, and C-substituted [RC(O)CH2-CB11H11]− carborate an...

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Bibliographic Details
Published inInorganics Vol. 12; no. 6; p. 173
Main Authors Barra, Vanessa C., Bernhardt, Eduard, Fellinger, Sarah, Jenne, Carsten, Langenbach, Shiomi S.
Format Journal Article
LanguageEnglish
Published Basel MDPI AG 01.06.2024
Subjects
acetamide
Alkynes
Ammonia
Anions
Boron
boron cluster
Carbon
carborate
Catalysts
closo-undecaborate
Copper
Infrared spectroscopy
Mass spectrometry
Mass spectroscopy
NMR
Nuclear magnetic resonance
Oxidation
Substitutes
Synthesis
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Summary:A new synthetic method for the synthesis of C-substituted [RC(O)CH2-CB11H11]− carborate anions has been developed. The reaction of [closo-B11H11]2− with terminal alkynes in the presence of a copper catalyst leads to insertion into the boron cluster, and C-substituted [RC(O)CH2-CB11H11]− carborate anions are formed. These reactions are strongly dependent on the reaction conditions, the solvents, and the alkynes used. The alkynes HCCCO2Et, HCCCO2Me, and HCCCONH2 lead to the formation of [NH2C(O)CH2-CB11H11]− as the final product in aqueous ammonia solution. In contrast, the reaction using the alkyne HCCCOMe yields [MeC(O)CH2-CB11H11]−. The products have been fully characterized by multinuclear NMR and IR spectroscopy as well as mass spectrometry. The crystal structures of K[NH2C(O)CH2-CB11H11] and [NEt3CH2Cl][NH2C(O)CH2-CB11H11] have been determined.
ISSN:2304-6740
2304-6740
DOI:10.3390/inorganics12060173