74492-44-7Relevant articles and documents
Frustrated Lewis Pair Catalyzed Dehydrogenative Oxidation of Indolines and Other Heterocycles
Maier, Alexander F. G.,Tussing, Sebastian,Schneider, Tobias,Fl?rke, Ulrich,Qu, Zheng -Wang,Grimme, Stefan,Paradies, Jan
supporting information, p. 12219 - 12223 (2016/10/13)
An acceptorless dehydrogenation of heterocycles catalyzed by frustrated Lewis pairs (FLPs) was developed. Oxidation with concomitant liberation of molecular hydrogen proceeded in high to excellent yields for N-protected indolines as well as four other substrate classes. The mechanism of this unprecedented FLP-catalyzed reaction was investigated by mechanistic studies, characterization of reaction intermediates by NMR spectroscopy and X-ray crystal analysis, and by quantum-mechanical calculations. Hydrogen liberation from the ammonium hydridoborate intermediate is the rate-determining step of the oxidation. The addition of a weaker Lewis acid as a hydride shuttle increased the reaction rate by a factor of 2.28 through a second catalytic cycle.
Forced nucleophilic substitution reaction of chlorobenzenes bearing electron-donating groups by the use of 'naked' methoxide anion
Fukui,Endo,Oishi
, p. 3639 - 3648 (2007/10/02)
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