JEFFREY M. FARRELLStephan, Douglas W.Douglas W.Stephan2022-05-272022-05-272015https://www.scopus.com/inward/record.uri?eid=2-s2.0-84941242127&doi=10.1039%2fc5cc06248a&partnerID=40&md5=a9089cafaca5f458af682f52b5b7c25ahttps://scholars.lib.ntu.edu.tw/handle/123456789/612096Sequential reaction of 2-lithio-1-methylimidazole with 9-borabicyclo[3.3.1]nonane (9-BBN) dimer and 9-Cl-9-BBN yields diboryl-N-heterocycle C4H5N2(H)(BC8H14)2 (1). Reaction of 1 with I2 results in the net substitution of chelated hydride for a singly boron-bound iodide to produce C4H5N2(I)(BC8H14)2 (2). Conversely, reaction of 1 with [Ph3C][B(C6F5)4] results in the formation of the bidentate cationic Lewis acid [(C4H5N2)(BC8H14)2][B(C6F5)4] (3). Compound 3 catalyzes the hydrogenation of N-benzylidene-tert-butylamine at room-temperature. ? 2015 The Royal Society of Chemistry.bicyclo[3.3.1]nonane derivative; boron; dimer; imidazole derivative; iodide; Lewis acid; Article; chemical reaction; hydrogenation; proton nuclear magnetic resonance; reaction time; room temperature; synthesis; X ray crystallographyjournal article10.1039/c5cc06248a2-s2.0-84941242127