@article{pittir17270, volume = {132}, number = {33}, month = {August}, author = {K Nozaki and Y Aramaki and M Yamashita and SH Ueng and M Malacria and E Lac{\^o}te and DP Curran}, title = {Boryltrihydroborate: Synthesis, structure, and reactivity as a reductant in ionic, organometallic, and radical reactions}, journal = {Journal of the American Chemical Society}, pages = {11449 -- 11451}, year = {2010}, url = {http://d-scholarship-dev.library.pitt.edu/17270/}, abstract = {Reaction of lithium 1,3-bis(2,6-diisopropylphenyl)-2,3-dihydro-1H-1,3,2- diazaborol-2-ide with borane?THF provides the first boryl-substituted borohydride: lithium [1,3-bis(2,6-diisopropylphenyl)-2,3-dihydro-1H-1,3,2- diazaborol-2-yl]trihydroborate. The compound is fully characterized by 11B, 1H, and 7Li NMR spectra and other means, and these data are compared to neutral and anionic benchmark compounds. The compound crystallizes as a dimer complexed to four THF molecules. The dimer lacks the bridging B-H bonds seen in neutral boranes and is instead held together by ionic Li - -HB interactions. A preliminary scan of reactions with several iodides shows that the compound participates in an ionic reduction (with a primary-alkyl iodide), an organometallic reduction (Pd-catalyzed with an aryl iodide), and a radical reduction (AIBN-initiated with a sugar-derived iodide). Accordingly the new borylborohydride class may share properties of both traditional borohydrides and isoelectronic N-heterocyclic carbene boranes. {\copyright} 2010 American Chemical Society.} }