Frustrated Lewis Pair Catalyzed Dehydrogenative Oxidation of Indolines and Other Heterocycles

• Published in: Angewandte Chemie International Edition Vol. 55; no. 40; pp. 12219 - 12223
• Main Authors: Maier, Alexander F. G., Tussing, Sebastian, Schneider, Tobias, Flörke, Ulrich, Qu, Zheng-Wang, Grimme, Stefan, Paradies, Jan
• Format: Journal Article
• Language: English
• Published: WEINHEIM Blackwell Publishing Ltd 26.09.2016; Wiley; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: 1,2-dihydroquinolines; 1,4-dihydropyridines; 2-dihydroquinolines; 4-dihydropyridines; acceptorless dehydrogenation; Ammonium; Catalysis; Chemistry; Chemistry, Multidisciplinary; Dehydrogenation; frustrated Lewis pairs; Heterocyclic compounds; Hydrogen storage; indolines; Intermediates; Lewis acid; Magnetic resonance spectroscopy; NMR spectroscopy; Oxidation; Physical Sciences; Reaction intermediates; Science & Technology; Spectroscopic analysis; indolines; AUXILIARY BASIS-SETS; FREE HYDROGEN ACTIVATION; NITROGEN-HETEROCYCLES; IMINES; 1,2-dihydroquinolines; B(C6F5)-CATALYZED TRANSFER; acceptorless dehydrogenation; DIHYDROGEN; TEMPERATURE; ZETA VALENCE QUALITY; 1,4-dihydropyridines; AMMONIA-BORANE DEHYDROGENATION; METAL-FREE; frustrated Lewis pairs

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 unprece...