Support influences in the Pd-catalyzed racemization and dynamic kinetic resolution of chiral benzylic amines
The acid-base properties of the supports for Pd catalysts strongly affect their performance in racemization and dynamic kinetic resolution (DKR) of chiral benzylic amines. The need for a basic support was proven by comparing the racemization results obtained for Pd on silica, on LDH (layered double...
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ftunivleuven:oai:lirias.kuleuven.be:123456789/258640 2023-05-15T14:02:22+02:00 Support influences in the Pd-catalyzed racemization and dynamic kinetic resolution of chiral benzylic amines Parvulescu, Andrei N Jacobs, Pierre De Vos, Dirk 2009-10 https://lirias.kuleuven.be/handle/123456789/258640 http://gateway.isiknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=DOISource&SrcApp=PRODUCT_NAME&KeyAID=10.1016%2Fj.apcata.2009.07.042&DestApp=DOI&SrcAppSID=APP_SID&SrcJTitle=WURS_TITLE en eng Elsevier science bv Applied catalysis a-general vol:368 issue:1-2 pages:9-16 https://lirias.kuleuven.be/handle/123456789/258640 0926-860X http://gateway.isiknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=DOISource&SrcApp=PRODUCT_NAME&KeyAID=10.1016%2Fj.apcata.2009.07.042&DestApp=DOI&SrcAppSID=APP_SID&SrcJTitle=WURS_TITLE pd catalysts basic supports chiral amine racemization dynamic kinetic resolution lipases enantiomerically pure amines layered double hydroxides secondary alcohols asymmetric transformations palladium catalysts hydrogen-peroxide ruthenium acylation optimization temperature Description (Metadata) only IT article 2009 ftunivleuven 2017-06-02T19:17:59Z The acid-base properties of the supports for Pd catalysts strongly affect their performance in racemization and dynamic kinetic resolution (DKR) of chiral benzylic amines. The need for a basic support was proven by comparing the racemization results obtained for Pd on silica, on LDH (layered double hydroxide) and on carbon. Pd on amine-functionalized silica proved to be more selective for the racemization of (S)-1-phenylethylamine than Pd on alkaline earth supports or Pd on LDH. The difference in selectivity between various Pd catalysts is determined by the rates of formation of the side products. The rate constants of side product formation processes were even higher in the case of Pd/SiO2 and Pd/C catalysts. The activity of the various catalysts for the rate determining amine dehydrogenation is similar when calculated per surface Pd atom. Combination of a Pd catalyst with Candida antarctica lipase B (Novozyme 435) for a one-pot DKR of 1-phenylethylamine gave the best results when Pd on 3-aminopropyl functionalized silica or Pd on 3-(1-piperazino)propyl functionalized silica were used as racemization catalysts, namely 93% yield of the corresponding (R)-amide, with 99% e.e. (C) 2009 Published by Elsevier B.V. status: published Article in Journal/Newspaper Antarc* Antarctica KU Leuven: Lirias |
institution |
Open Polar |
collection |
KU Leuven: Lirias |
op_collection_id |
ftunivleuven |
language |
English |
topic |
pd catalysts basic supports chiral amine racemization dynamic kinetic resolution lipases enantiomerically pure amines layered double hydroxides secondary alcohols asymmetric transformations palladium catalysts hydrogen-peroxide ruthenium acylation optimization temperature |
spellingShingle |
pd catalysts basic supports chiral amine racemization dynamic kinetic resolution lipases enantiomerically pure amines layered double hydroxides secondary alcohols asymmetric transformations palladium catalysts hydrogen-peroxide ruthenium acylation optimization temperature Parvulescu, Andrei N Jacobs, Pierre De Vos, Dirk Support influences in the Pd-catalyzed racemization and dynamic kinetic resolution of chiral benzylic amines |
topic_facet |
pd catalysts basic supports chiral amine racemization dynamic kinetic resolution lipases enantiomerically pure amines layered double hydroxides secondary alcohols asymmetric transformations palladium catalysts hydrogen-peroxide ruthenium acylation optimization temperature |
description |
The acid-base properties of the supports for Pd catalysts strongly affect their performance in racemization and dynamic kinetic resolution (DKR) of chiral benzylic amines. The need for a basic support was proven by comparing the racemization results obtained for Pd on silica, on LDH (layered double hydroxide) and on carbon. Pd on amine-functionalized silica proved to be more selective for the racemization of (S)-1-phenylethylamine than Pd on alkaline earth supports or Pd on LDH. The difference in selectivity between various Pd catalysts is determined by the rates of formation of the side products. The rate constants of side product formation processes were even higher in the case of Pd/SiO2 and Pd/C catalysts. The activity of the various catalysts for the rate determining amine dehydrogenation is similar when calculated per surface Pd atom. Combination of a Pd catalyst with Candida antarctica lipase B (Novozyme 435) for a one-pot DKR of 1-phenylethylamine gave the best results when Pd on 3-aminopropyl functionalized silica or Pd on 3-(1-piperazino)propyl functionalized silica were used as racemization catalysts, namely 93% yield of the corresponding (R)-amide, with 99% e.e. (C) 2009 Published by Elsevier B.V. status: published |
format |
Article in Journal/Newspaper |
author |
Parvulescu, Andrei N Jacobs, Pierre De Vos, Dirk |
author_facet |
Parvulescu, Andrei N Jacobs, Pierre De Vos, Dirk |
author_sort |
Parvulescu, Andrei N |
title |
Support influences in the Pd-catalyzed racemization and dynamic kinetic resolution of chiral benzylic amines |
title_short |
Support influences in the Pd-catalyzed racemization and dynamic kinetic resolution of chiral benzylic amines |
title_full |
Support influences in the Pd-catalyzed racemization and dynamic kinetic resolution of chiral benzylic amines |
title_fullStr |
Support influences in the Pd-catalyzed racemization and dynamic kinetic resolution of chiral benzylic amines |
title_full_unstemmed |
Support influences in the Pd-catalyzed racemization and dynamic kinetic resolution of chiral benzylic amines |
title_sort |
support influences in the pd-catalyzed racemization and dynamic kinetic resolution of chiral benzylic amines |
publisher |
Elsevier science bv |
publishDate |
2009 |
url |
https://lirias.kuleuven.be/handle/123456789/258640 http://gateway.isiknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=DOISource&SrcApp=PRODUCT_NAME&KeyAID=10.1016%2Fj.apcata.2009.07.042&DestApp=DOI&SrcAppSID=APP_SID&SrcJTitle=WURS_TITLE |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
Applied catalysis a-general vol:368 issue:1-2 pages:9-16 https://lirias.kuleuven.be/handle/123456789/258640 0926-860X http://gateway.isiknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=DOISource&SrcApp=PRODUCT_NAME&KeyAID=10.1016%2Fj.apcata.2009.07.042&DestApp=DOI&SrcAppSID=APP_SID&SrcJTitle=WURS_TITLE |
_version_ |
1766272601011781632 |