Cyanide ion complexation by a cationic borane in aqueous media

INOR 785

Todd W. Hudnall, thudnall@mail.chem.tamu.edu and François P. Gabbaï, gabbai@mail.chem.tamu.edu. Department of Chemistry, Texas A&M University, MS 3255, College Station, TX 77843-3255
Recently, our group has reported that the ammonium triarylborane [1]+ is able to capture fluoride ions from water under biphasic conditions. In an effort to understand the parameters that govern the fluoride ion affinity of such receptors, we have now decided to synthesize and study other ammonium boranes. In this presentation, we will show that reaction of 4-(dimesitylboryl)-N,N-dimethylaniline with methyl triflate affords the novel ammonium borane 4-(dimesitylboryl)-N,N,N-trimethylbenzenaminium as a triflate salt ([2]OTf). This new cationic borane reacts with both fluoride and cyanide in organic solvents to afford the corresponding ammonium fluoroborate and ammonium cyanoborate zwitterions. Remarkably, [2]+ is selective for cyanide in aqueous media.