Hydrogenations at Room Temperature and Atmospheric Pressure with Mesoionic Carbene-Stabilized Borenium Catalysts

1,2,3‐Triazolylidene‐based mesoionic carbene boranes have been synthesized in a convenient one‐pot protocol from the corresponding 1,2,3‐triazolium salts, base, and borane. Borenium ions are obtained by hydride ion and serve as catalysts in mild hydrogenation reactions of imines and unsaturated N‐he...

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Published inAngewandte Chemie International Edition Vol. 54; no. 8; pp. 2467 - 2471
Main Authors Eisenberger, Patrick, Bestvater, Brian P., Keske, Eric C., Crudden, Cathleen M.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 16.02.2015
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Ambient temperature
Atmospheric Pressure
Boranes
Boranes - chemistry
borenium
Catalysis
Catalysts
Chemistry
Chemistry, Multidisciplinary
Crystallography, X-Ray
Hydrogenation
Imines
Lewis acids
Lewis Acids - chemistry
mesoionic carbenes
Methane - analogs & derivatives
Methane - chemistry
Molecular Conformation
Physical Sciences
Pressure
Science & Technology
Temperature
Triazoles - chemistry
Unsaturated
mesoionic carbenes
borenium
N-HETEROCYCLIC CARBENE
ACTIVATION
IMINES
Lewis acids
REACTIVITY
catalysis
FRUSTRATED LEWIS PAIRS
BORANE
hydrogenation
LIGANDS
CHEMISTRY
ASYMMETRIC HYDROGENATION
ACIDITY
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Summary:1,2,3‐Triazolylidene‐based mesoionic carbene boranes have been synthesized in a convenient one‐pot protocol from the corresponding 1,2,3‐triazolium salts, base, and borane. Borenium ions are obtained by hydride ion and serve as catalysts in mild hydrogenation reactions of imines and unsaturated N‐heterocycles at ambient pressure and temperature. Size does matter after all: Tunable, comparatively robust mesoionic borenium ions catalyze the mild hydrogenation of N‐containing unsaturated organic functionalities at ambient temperature and ambient pressure. These reactions proceed through a mechanism reminiscent of frustrated Lewis pair chemistry.
Bibliography:Queen's University
The Natural Sciences and Engineering Research Council of Canada (NSERC) is gratefully acknowledged in terms of operating, equipment, accelerator, and strategic grants to C.M.C. J. Lu and Dr. G. Schatte are thanked for the single-crystal studies. J. Song is thanked for experimental contributions and Dr. K. Itami is thanked for useful suggestions. E.C.K. thanks NSERC for a PGSD scholarship. E.C.K. and B.P.B. thank Queen's University for QGS Fellowships.
Natural Sciences and Engineering Research Council of Canada (NSERC)
ArticleID:ANIE201409250
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The Natural Sciences and Engineering Research Council of Canada (NSERC) is gratefully acknowledged in terms of operating, equipment, accelerator, and strategic grants to C.M.C. J. Lu and Dr. G. Schatte are thanked for the single‐crystal studies. J. Song is thanked for experimental contributions and Dr. K. Itami is thanked for useful suggestions. E.C.K. thanks NSERC for a PGSD scholarship. E.C.K. and B.P.B. thank Queen’s University for QGS Fellowships.
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SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201409250