Tandem synthesis of tetrahydroquinolines and identification of the reaction network by operando NMR

dc.contributor.author Chen, Jingwen
dc.contributor.author Qi, Long
dc.contributor.author Zhang, Biying
dc.contributor.author Huang, Wenyu
dc.contributor.author Chen, Minda
dc.contributor.author Kobayashi, Takeshi
dc.contributor.author Bao, Zongbi
dc.contributor.author Yang, Qiwei
dc.contributor.author Ren, Qilong
dc.contributor.author Huang, Wenyu
dc.contributor.author Zhang, Zhiguo
dc.contributor.department Ames Laboratory
dc.contributor.department Chemistry
dc.date 2021-06-24T19:31:23.000
dc.date.accessioned 2021-08-14T01:37:05Z
dc.date.available 2021-08-14T01:37:05Z
dc.date.embargo 2022-04-20
dc.date.issued 2021-04-20
dc.description.abstract <p>The study of the reaction mechanism and complex network for heterogeneously catalyzed tandem reactions is challenging but can guide reaction design and optimization. Here, we describe a case study using bifunctional metal–organic framework supported Pd nanoparticles (Pd/UiO-66(HCl)) for the one-pot tandem synthesis of substituted tetrahydroquinolines via the Claisen–Schmidt condensation and reductive intramolecular cyclization. The directly observed evolution of intermediates and products, including reactive species containing hydroxylamine group and unstable intermediate 2-phenyl-3,4-dihydroquinoline, was enabled by operando magic angle spinning nuclear magnetic resonance studies under 50 bar H2. The reaction network of the tandem reaction is deduced based on reaction kinetic information obtained from the operando study. The optimized procedure was applied to various acetophenone and nitrobenzaldehyde derivatives carrying different functional groups, and eight valuable substituted tetrahydroquinolines were obtained in moderate to good yields. This work provides a molecular-level understanding of the catalytic system and brings up new opportunities for efficient and sustainable synthesis of medicinally relevant building blocks.</p>
dc.identifier archive/lib.dr.iastate.edu/ameslab_manuscripts/917/
dc.identifier.articleid 1930
dc.identifier.contextkey 23509741
dc.identifier.s3bucket isulib-bepress-aws-west
dc.identifier.submissionpath ameslab_manuscripts/917
dc.identifier.uri https://dr.lib.iastate.edu/handle/20.500.12876/kv7kyB5v
dc.language.iso en
dc.relation.ispartofseries IS-J 10504
dc.source.bitstream archive/lib.dr.iastate.edu/ameslab_manuscripts/917/IS_J_10504.pdf|||Sat Jan 15 02:29:12 UTC 2022
dc.source.uri 10.1039/D1CY00418B
dc.subject.disciplines Catalysis and Reaction Engineering
dc.title Tandem synthesis of tetrahydroquinolines and identification of the reaction network by operando NMR
dc.type article
dc.type.genre article
dspace.entity.type Publication
relation.isAuthorOfPublication 6acd59cc-28ec-46dd-8bf0-51bcc56d79f9
relation.isOrgUnitOfPublication 25913818-6714-4be5-89a6-f70c8facdf7e
relation.isOrgUnitOfPublication 42864f6e-7a3d-4be3-8b5a-0ae3c3830a11
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