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Pyridine Adducts of Tricyano‐ and Dicyanoboranes

European journal of organic chemistry(2023)

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摘要
Cyanoborane adducts of the Lewis acids B(CN)(3), BF(CN)(2), and BH(CN)(2) with pyridine and 4-cyanopyridine have been obtained in high yields. The syntheses were accomplished by oxidation of the readily available potassium salts of the cyano(hydrido)borate anions [BH(CN)(3)](-) (MHB), [BFH(CN)(2)](-) (FHB), and [BH2(CN)(2)](-) (DHB) with bromine in the presence of the respective pyridine derivative C5H5N or 4-CN-C5H4N as starting material. All six cyanoborane adducts have been characterized by NMR and vibrational spectroscopy, elemental analysis, and single-crystal X-ray diffraction. The reduction of the cyanoborane adducts has been investigated by cyclic voltammetry and the Lewis acidity of the different cyanoboranes has been assessed using the Gutmann-Beckett method. Selected experimental data and trends are compared to theoretical ones, for example fluoride ion affinities (FIAs).
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关键词
boranes,cyanoboranes,cyanide,Lewis acids,pyridines
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