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Heterogeneous catalyzed chemoselective reductive amination of halogenated aromatic aldehydes

(2021) CHEMCATCHEM. 13(13). p.3021-3026
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Abstract
The chemoselective conversion of a specific functional group in a multifunctional substrate is of great importance in the chemical industry to obtain cost efficient, sustainable and waste free processes. This work focuses on the chemoselective amination of halogenated aromatic aldehydes with dimethyl amine towards halogenated aromatic amines, a raw material used in the production of for example agrochemical active ingredients. It was found that by combining palladium, a metal known for dehalogenation reactions, and copper, known for its direct hydrogenation of aldehydes to alcohols, in one heterogeneous bimetallic catalyst, a synergistic effect is obtained. By depositing copper onto a palladium on carbon catalyst with a Cu/Pd ratio of at least 1 : 1, the yield could be increased from 66 % (Pd/C) to 98 % (PdCu/C). Moreover, this highly active and stable catalyst also showed suppressed dehalogenation side-reactions in several other chemical conversions such as hydrogenation of nitro functional groups and hydrogenation of aldehydes.
Keywords
Inorganic Chemistry, Organic Chemistry, Physical and Theoretical Chemistry, Catalysis, alloy formation, chemoselectivity, dehalogenation, heterogeneous catalysis, reductive amination, SELECTIVE HYDROGENATION, PALLADIUM-RUTHENIUM, LIQUID-PHASE, PD, SILICA, GOLD, QUINOLINE, AG

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MLA
Dumoleijn, Kim, et al. “Heterogeneous Catalyzed Chemoselective Reductive Amination of Halogenated Aromatic Aldehydes.” CHEMCATCHEM, vol. 13, no. 13, 2021, pp. 3021–26, doi:10.1002/cctc.202100334.
APA
Dumoleijn, K., Villa, A., Marelli, M., Prati, L., Moonen, K., & Stevens, C. (2021). Heterogeneous catalyzed chemoselective reductive amination of halogenated aromatic aldehydes. CHEMCATCHEM, 13(13), 3021–3026. https://doi.org/10.1002/cctc.202100334
Chicago author-date
Dumoleijn, Kim, Alberto Villa, Marcello Marelli, Laura Prati, Kristof Moonen, and Christian Stevens. 2021. “Heterogeneous Catalyzed Chemoselective Reductive Amination of Halogenated Aromatic Aldehydes.” CHEMCATCHEM 13 (13): 3021–26. https://doi.org/10.1002/cctc.202100334.
Chicago author-date (all authors)
Dumoleijn, Kim, Alberto Villa, Marcello Marelli, Laura Prati, Kristof Moonen, and Christian Stevens. 2021. “Heterogeneous Catalyzed Chemoselective Reductive Amination of Halogenated Aromatic Aldehydes.” CHEMCATCHEM 13 (13): 3021–3026. doi:10.1002/cctc.202100334.
Vancouver
1.
Dumoleijn K, Villa A, Marelli M, Prati L, Moonen K, Stevens C. Heterogeneous catalyzed chemoselective reductive amination of halogenated aromatic aldehydes. CHEMCATCHEM. 2021;13(13):3021–6.
IEEE
[1]
K. Dumoleijn, A. Villa, M. Marelli, L. Prati, K. Moonen, and C. Stevens, “Heterogeneous catalyzed chemoselective reductive amination of halogenated aromatic aldehydes,” CHEMCATCHEM, vol. 13, no. 13, pp. 3021–3026, 2021.
@article{8751890,
  abstract     = {{The chemoselective conversion of a specific functional group in a multifunctional substrate is of great importance in the chemical industry to obtain cost efficient, sustainable and waste free processes. This work focuses on the chemoselective amination of halogenated aromatic aldehydes with dimethyl amine towards halogenated aromatic amines, a raw material used in the production of for example agrochemical active ingredients. It was found that by combining palladium, a metal known for dehalogenation reactions, and copper, known for its direct hydrogenation of aldehydes to alcohols, in one heterogeneous bimetallic catalyst, a synergistic effect is obtained. By depositing copper onto a palladium on carbon catalyst with a Cu/Pd ratio of at least 1 : 1, the yield could be increased from 66 % (Pd/C) to 98 % (PdCu/C). Moreover, this highly active and stable catalyst also showed suppressed dehalogenation side-reactions in several other chemical conversions such as hydrogenation of nitro functional groups and hydrogenation of aldehydes.}},
  author       = {{Dumoleijn, Kim and Villa, Alberto and Marelli, Marcello and Prati, Laura and Moonen, Kristof and Stevens, Christian}},
  issn         = {{1867-3880}},
  journal      = {{CHEMCATCHEM}},
  keywords     = {{Inorganic Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Catalysis,alloy formation,chemoselectivity,dehalogenation,heterogeneous catalysis,reductive amination,SELECTIVE HYDROGENATION,PALLADIUM-RUTHENIUM,LIQUID-PHASE,PD,SILICA,GOLD,QUINOLINE,AG}},
  language     = {{eng}},
  number       = {{13}},
  pages        = {{3021--3026}},
  title        = {{Heterogeneous catalyzed chemoselective reductive amination of halogenated aromatic aldehydes}},
  url          = {{http://dx.doi.org/10.1002/cctc.202100334}},
  volume       = {{13}},
  year         = {{2021}},
}

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