Synthesis of a diboryl-N-heterocycle and its conversion to a bidentate cationic Lewis acid
Journal
CHEMICAL COMMUNICATIONS
Journal Volume
51
Journal Issue
76
Pages
14322-14325
Date Issued
2015
Author(s)
Stephan, Douglas W.
Abstract
Sequential 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.
Other Subjects
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 crystallography
Type
journal article