Reactions of nucleophilic addition of primary amines to the nitrilium derivative of the closo-decaborate anion [2-B10H9(N≡CCH3)]−

Synthesis of Boronated Amidines by Addition of Amines to Nitrilium Derivative of Cobalt Bis(Dicarbollide)

“…Of particular interest are the reactions of nitriles with amines in the presence of transition metal complexes, which can be used both in a stoichiometric ratio to study the reactions of coordinated nitriles [31,32], and in catalytic amounts in organic synthesis [69][70][71]. Synthesis of boronated amidines by the reaction of nucleophilic addition of amines to alkylnitrilium derivatives was first described for arachno-decaborate [72] and closo-decaborate [40,41,[73][74][75][76] anions. Later, amidines on the base of nido-carborane [77][78][79] and the closo-dodecaborate anion [80] were synthesized.…”

“…Nucleophilic addition reactions to the highly polarized -N + ≡CR triple bonds in aryl-and alkylnitrilium salts [30] and nitrile complexes of transition metals [31][32][33][34][35] are widely used in organic synthesis and have large potential in the modification of polyhedral boron hydrides [36]. Thus, the nitrilium derivatives of the closo-decaborate anion react with water [37,38], alcohols [39], amines [40,41], hydrazines [42], hydrazones [42] and oximes [43,44], as well as with various carbanions [45,46] to form the corresponding addition products. Like organic nitrilium salts, they are able to participate in 1,3-dipolar cycloaddition reactions with azides and nitrones leading to the corresponding boronated tetrazoles [47] and 2,3-dihydro-1,2,4-oxadiazoles [48], respectively.…”

Synthesis of New Bioinorganic Systems Based on Nitrilium Derivatives of closo-Decaborate Anion and meso-Arylporphyrins with Pendant Amino Groups

“…[13][14][15][16][17][18] Previously we discovered convenient method of synthesis of disubstituted oxonium derivatives using CF 3 SO 3 H as electrophilic inductor. [19] This method is quite universal and allows to produce disubstituted derivatives containing various exo-polyhedral bonds.…”

New Method for Synthesis of Substituted N-Borylated Dipeptides Based on Acetonitrile Derivative of the closo-Dodecaborate Anion

“…It was previously shown that the addition of nucleophilic reagents of various natures to nitrile functional groups in anionic boron clusters can be considered as a convenient way of directed synthesis of their substituted derivatives [12][13][14][15][16][17][18][19][20][21][22][23][24], including those based on biologically active substances [6,25] and biomimetic systems [26,27]. It was found that the addition of tertbutyl esters of proteinogenic amino acids to nitrile derivatives of the closo-decaborate anion and their subsequent selective hydrolysis is a convenient method for the preparation of N-borylated peptides [28].…”