B(C₆F₅)₃‐katalysierte Hydrierung von Oximethern ohne Spaltung der N‐O‐Bindung

Abstract

Die Hydrierung von Oximen und Oximethern geht normalerweise mit der Spaltung der N-O-Bindung einher und setzt daher Amine und eben nicht Hydroxylamine frei. Die Bor-Lewis-Säure B(C 6 F 5 ) 3 katalysiert die chemoselektive Hydrierung von Oximethern bei erhçhter oder sogar Raumtemperatur unter 100 bar Wasserstoffdruck. Die Verwendung der Triisopropylsilylgruppe als Schutzgruppe erlaubt eine mühe-lose Freisetzung der Hydroxylamine.

Indium Tribromide‐Catalysed Transfer‐Hydrogenation: Expanding the Scope of the Hydrogenation and of the Regiodivergent DH or HD Addition to Alkenes

“…[ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 ] Based on these characteristics, dihydroaromatic compounds have found various applications[ 10 , 11 , 12 , 13 , 14 , 15 ] and the use as a surrogate for molecular hydrogen is one of the most prominent examples. [ 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 ] Other applications of substituted 1,4‐cyclohexadienes are the transfer of HBr, [24] HCN[ 25 , 26 ] and many other hydrofunctionalisation reactions to transfer various groups[ 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 ] to unsaturated starting materials, which have been summarised recently. [ 36 , 37 , 38 , 39 ]…”

“…[1][2][3][4][5][6][7][8][9] Based on these characteristics, dihydroaromatic compounds have found various applications [10][11][12][13][14][15] and the use as a surrogate for molecular hydrogen is one of the most prominent examples. [16][17][18][19][20][21][22][23] Other applications of substituted 1,4-cyclohexadienes are the transfer of HBr, [24] HCN [25,26] and many other hydrofunctionalisation reactions to transfer various groups [27][28][29][30][31][32][33][34][35] to unsaturated starting materials, which have been summarised recently. [36][37][38][39] The Oestreich group pioneered in the regioselective hydrodeuterogenation of 1,1-diarylalkenes in 2018 by using an unsymmetrical surrogate where the hydrogen and the deuterium atoms are bound differently, so that the hydrogen acts as a hydride equivalent (H + ) and the deuterium atom as a "heavy" proton (D À ).…”

“…Dihydroaromatic compounds are relatively sensitive towards air and other mild oxidising agents and can be converted easily into the corresponding arenes [1–9] . Based on these characteristics, dihydroaromatic compounds have found various applications [10–15] and the use as a surrogate for molecular hydrogen is one of the most prominent examples [16–23] . Other applications of substituted 1,4‐cyclohexadienes are the transfer of HBr, [24] HCN [25,26] and many other hydrofunctionalisation reactions to transfer various groups [27–35] to unsaturated starting materials, which have been summarised recently [36–39] …”