Frustrated Lewis Pair Catalyzed Dehydrogenative Oxidation of Indolines and Other Heterocycles

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...

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Published inAngewandte 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
LanguageEnglish
Published WEINHEIM Blackwell Publishing Ltd 26.09.2016
Wiley
Wiley Subscription Services, Inc
EditionInternational 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
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Abstract 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. The acceptorless dehydrogenation of N‐protected indolines and other heterocycles is catalyzed by frustrated Lewis pairs. Mechanistic as well as quantum‐mechanical studies revealed the liberation of molecular hydrogen to be the rate‐determining step. The addition of a weaker Lewis acid as a hydride shuttle increased the reaction rate by a factor of 2.28.
AbstractList 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.
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. The acceptorless dehydrogenation of N‐protected indolines and other heterocycles is catalyzed by frustrated Lewis pairs. Mechanistic as well as quantum‐mechanical studies revealed the liberation of molecular hydrogen to be the rate‐determining step. The addition of a weaker Lewis acid as a hydride shuttle increased the reaction rate by a factor of 2.28.
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.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.
Author Schneider, Tobias
Tussing, Sebastian
Paradies, Jan
Grimme, Stefan
Maier, Alexander F. G.
Flörke, Ulrich
Qu, Zheng-Wang
Author_xml – sequence: 1
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  surname: Maier
  fullname: Maier, Alexander F. G.
  organization: Institute of Organic Chemistry, University of Paderborn, Warburger Strasse 100, 33098, Paderborn, Germany
– sequence: 2
  givenname: Sebastian
  surname: Tussing
  fullname: Tussing, Sebastian
  organization: Institute of Organic Chemistry, University of Paderborn, Warburger Strasse 100, 33098, Paderborn, Germany
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  givenname: Tobias
  surname: Schneider
  fullname: Schneider, Tobias
  organization: Institute of Organic Chemistry, University of Paderborn, Warburger Strasse 100, 33098, Paderborn, Germany
– sequence: 4
  givenname: Ulrich
  surname: Flörke
  fullname: Flörke, Ulrich
  organization: Institute of Inorganic Chemistry, University of Paderborn, Warburger Strasse 100, 33098, Paderborn, Germany
– sequence: 5
  givenname: Zheng-Wang
  surname: Qu
  fullname: Qu, Zheng-Wang
  organization: Mulliken Center for Theoretical Chemistry, Institut für Physikalische und Theoretische Chemie, University of Bonn, Beringstrasse 4, 53115, Bonn, Germany
– sequence: 6
  givenname: Stefan
  surname: Grimme
  fullname: Grimme, Stefan
  email: grimme@thch.uni-bonn.de
  organization: Mulliken Center for Theoretical Chemistry, Institut für Physikalische und Theoretische Chemie, University of Bonn, Beringstrasse 4, 53115, Bonn, Germany
– sequence: 7
  givenname: Jan
  surname: Paradies
  fullname: Paradies, Jan
  email: jan.paradies@uni-paderborn.de
  organization: Institute of Organic Chemistry, University of Paderborn, Warburger Strasse 100, 33098, Paderborn, Germany
BackLink https://www.ncbi.nlm.nih.gov/pubmed/27594431$$D View this record in MEDLINE/PubMed
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Issue 40
Keywords 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
Language English
License http://onlinelibrary.wiley.com/termsAndConditions#vor
2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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Notes German science foundation (DFG) - No. PA 1562/6-1
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PublicationTitle Angewandte Chemie International Edition
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Publisher Blackwell Publishing Ltd
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2013; 4
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1993
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1961; 32
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Greb, L (WOS:000309181700039) 2012; 51
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Paul, A (WOS:000250966100007) 2007; 46
Grimme, S (WOS:000359377200011) 2015; 143
Tussing, S (WOS:000354651300014) 2015; 21
Custelcean, R (WOS:000170045000005) 2001; 101
Greb, L (WOS:000319741100039) 2013; 52
Appelt, C (WOS:000317064600036) 2013; 52
Tussing, S (WOS:000379727900018) 2016; 22
Wong, OA (WOS:000259119300009) 2008; 108
Scott, DJ (WOS:000344906100002) 2014; 136
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Tao, JM (WOS:000185719500032) 2003; 91
Farrell, JM (WOS:000294647500008) 2011; 30
Paradies, J (WOS:000337176800002) 2014; 53
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Greb, L (WOS:000330775900023) 2014; 50
Chatterjee, I (WOS:000349209200056) 2015; 54
Appelt, C. (000384713700009.5) 2013; 125
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Heiden, ZM (WOS:000355382500006) 2015; 34
Yamaguchi, R (WOS:000267630000035) 2009; 131
Himmelberger, DW (WOS:000270433900047) 2009; 131
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Chatterjee, I. (000384713700009.7) 2015; 127
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Eckert, F. (000384713700009.18) 2013
Keess, S (WOS:000349943200014) 2015; 34
Koski, W. S. (000384713700009.38) 1961; 32
Dobereiner, GE (WOS:000274705900005) 2010; 110
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Stephan, DW (WOS:000359962000001) 2015; 137
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Snippet An acceptorless dehydrogenation of heterocycles catalyzed by frustrated Lewis pairs (FLPs) was developed. Oxidation with concomitant liberation of molecular...
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SubjectTerms 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
Title Frustrated Lewis Pair Catalyzed Dehydrogenative Oxidation of Indolines and Other Heterocycles
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