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  4. Synthesis of a diboryl-N-heterocycle and its conversion to a bidentate cationic Lewis acid
 
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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)
JEFFREY M. FARRELL  
Stephan, Douglas W.
DOI
10.1039/c5cc06248a
URI
https://www.scopus.com/inward/record.uri?eid=2-s2.0-84941242127&doi=10.1039%2fc5cc06248a&partnerID=40&md5=a9089cafaca5f458af682f52b5b7c25a
https://scholars.lib.ntu.edu.tw/handle/123456789/612096
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

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