| Autor: |
Jan Paradies, Tobias Schneider, Alexander F. G. Maier, Sebastian Tussing, Ulrich Flörke, Stefan Grimme, Zheng-Wang Qu |
| Rok vydání: |
2016 |
| Předmět: |
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| Zdroj: |
Angewandte Chemie International Edition. 55:12219-12223 |
| ISSN: |
1433-7851 |
| DOI: |
10.1002/anie.201606426 |
| Popis: |
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. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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