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Reductive imino-pinacol coupling reaction of halogenated aromatic imines and iminium ions catalyzed by precious metal catalysts using hydrogen

(2021) JOURNAL OF CATALYSIS. 400. p.103-113
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Abstract
The first heterogeneously catalyzed process for the reductive coupling of imines and iminium ions is reported using precious metal catalysts in combination with hydrogen gas as the terminal reductant. The optimized method in terms of catalyst composition and reaction conditions allowed to produce aro-matic vicinal diamines without the use of stoichiometric amounts of zero or low valent metals, which is currently the preferred method. The most important mechanistic features of the reaction were unraveled by a combined experimental and computational approach. The developed methodology is very efficient for the coupling of aromatic iminium ions with yields up to 88% while imines give only low to moderate yields. (c) 2021 Elsevier Inc. All rights reserved.
Keywords
Physical and Theoretical Chemistry, Catalysis, Heterogeneous catalysis, Imino-pinacol coupling reaction, Precious metal catalyst, Vicinal diamines, ALDIMINES, DIMERIZATION, CARBONYL, MECHANISM, ALDEHYDES, KETONES, INDIUM, ZINC

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MLA
Dumoleijn, Kim, et al. “Reductive Imino-Pinacol Coupling Reaction of Halogenated Aromatic Imines and Iminium Ions Catalyzed by Precious Metal Catalysts Using Hydrogen.” JOURNAL OF CATALYSIS, vol. 400, 2021, pp. 103–13, doi:10.1016/j.jcat.2021.05.023.
APA
Dumoleijn, K., Van Den Broeck, E., Stavinoha, J., Van Speybroeck, V., Moonen, K., & Stevens, C. (2021). Reductive imino-pinacol coupling reaction of halogenated aromatic imines and iminium ions catalyzed by precious metal catalysts using hydrogen. JOURNAL OF CATALYSIS, 400, 103–113. https://doi.org/10.1016/j.jcat.2021.05.023
Chicago author-date
Dumoleijn, Kim, Elias Van Den Broeck, J. Stavinoha, Veronique Van Speybroeck, K. Moonen, and Christian Stevens. 2021. “Reductive Imino-Pinacol Coupling Reaction of Halogenated Aromatic Imines and Iminium Ions Catalyzed by Precious Metal Catalysts Using Hydrogen.” JOURNAL OF CATALYSIS 400: 103–13. https://doi.org/10.1016/j.jcat.2021.05.023.
Chicago author-date (all authors)
Dumoleijn, Kim, Elias Van Den Broeck, J. Stavinoha, Veronique Van Speybroeck, K. Moonen, and Christian Stevens. 2021. “Reductive Imino-Pinacol Coupling Reaction of Halogenated Aromatic Imines and Iminium Ions Catalyzed by Precious Metal Catalysts Using Hydrogen.” JOURNAL OF CATALYSIS 400: 103–113. doi:10.1016/j.jcat.2021.05.023.
Vancouver
1.
Dumoleijn K, Van Den Broeck E, Stavinoha J, Van Speybroeck V, Moonen K, Stevens C. Reductive imino-pinacol coupling reaction of halogenated aromatic imines and iminium ions catalyzed by precious metal catalysts using hydrogen. JOURNAL OF CATALYSIS. 2021;400:103–13.
IEEE
[1]
K. Dumoleijn, E. Van Den Broeck, J. Stavinoha, V. Van Speybroeck, K. Moonen, and C. Stevens, “Reductive imino-pinacol coupling reaction of halogenated aromatic imines and iminium ions catalyzed by precious metal catalysts using hydrogen,” JOURNAL OF CATALYSIS, vol. 400, pp. 103–113, 2021.
@article{8717579,
  abstract     = {{The first heterogeneously catalyzed process for the reductive coupling of imines and iminium ions is reported using precious metal catalysts in combination with hydrogen gas as the terminal reductant. The optimized method in terms of catalyst composition and reaction conditions allowed to produce aro-matic vicinal diamines without the use of stoichiometric amounts of zero or low valent metals, which is currently the preferred method. The most important mechanistic features of the reaction were unraveled by a combined experimental and computational approach. The developed methodology is very efficient for the coupling of aromatic iminium ions with yields up to 88% while imines give only low to moderate yields. (c) 2021 Elsevier Inc. All rights reserved.}},
  author       = {{Dumoleijn, Kim and Van Den Broeck, Elias and Stavinoha, J. and Van Speybroeck, Veronique and Moonen, K. and Stevens, Christian}},
  issn         = {{0021-9517}},
  journal      = {{JOURNAL OF CATALYSIS}},
  keywords     = {{Physical and Theoretical Chemistry,Catalysis,Heterogeneous catalysis,Imino-pinacol coupling reaction,Precious metal catalyst,Vicinal diamines,ALDIMINES,DIMERIZATION,CARBONYL,MECHANISM,ALDEHYDES,KETONES,INDIUM,ZINC}},
  language     = {{eng}},
  pages        = {{103--113}},
  title        = {{Reductive imino-pinacol coupling reaction of halogenated aromatic imines and iminium ions catalyzed by precious metal catalysts using hydrogen}},
  url          = {{http://dx.doi.org/10.1016/j.jcat.2021.05.023}},
  volume       = {{400}},
  year         = {{2021}},
}

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