Publication:
Anion–cation synergistic metal-free catalytic oxidative homocoupling of benzylamines by triazolium iodide salts

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cris.virtual.author-orcid#PLACEHOLDER_PARENT_METADATA_VALUE#
cris.virtual.author-orcid0000-0001-7403-2329
cris.virtualsource.author-orcid57f3ec8b-dcd6-4577-b59e-68eef9acb1c2
cris.virtualsource.author-orcid7fd318c7-e95c-41d5-9428-9ed73b645156
dc.contributor.authorByrne, Joseph Peter
dc.contributor.authorAlbrecht, Martin
dc.date.accessioned2024-09-02T16:48:14Z
dc.date.available2024-09-02T16:48:14Z
dc.date.issued2020-09-04
dc.description.abstractTriazolium iodide salts are excellent catalysts for the selective oxidative coupling of benzylamines to yield imines. This metal-free reaction proceeds in quantitative spectroscopic yields when run in refluxing 1,2-dichlorobenzene and open to the air. No catalytic activity was observed with related triazolium tetrafluoroborate salts. Variation of catalyst and reaction atmosphere provides mechanistic insights, and revealed dioxygen as the terminal oxidant and the iodine/iodide couple as key redox component in the catalytic dehydrogenation pathway. While molecular iodine is competent as a catalyst in its own right, the triazolium cation triples the reaction rate and reaches turnover frequencies up to 30 h−1, presumably through beneficial interactions of the electron-poor azolium π system and I2, which facilitate the electron transfer from the substrate to iodine and concomitant formation of I−. This acceleration is specific for triazolium cations and represents a hybrid anion/cation catalytic process as a simple and straightforward route towards imine products, with economic advantages over previously reported metal-based catalytic systems.
dc.description.numberOfPages9
dc.description.sponsorshipDepartement für Chemie und Biochemie (DCB)
dc.identifier.doi10.48350/151062
dc.identifier.publisherDOI10.1039/D0OB01472A
dc.identifier.urihttps://boris-portal.unibe.ch/handle/20.500.12422/39507
dc.language.isoen
dc.publisherRoyal Society of Chemistry
dc.relation.ispartofOrganic & biomolecular chemistry
dc.relation.issn1477-0520
dc.relation.organizationDCD5A442C14DE17DE0405C82790C4DE2
dc.relation.projectExploiting carbohydrate/N-heterocyclic carbene hybrid complexes as innovative multifunctional oxidation catalysts with tailoring of weak interactions allowing for development of enzyme mimics
dc.relation.projectExploiting Synergistic Properties of Mesoionic Carbene Complexes: Teaching Rusty Metals Challenging Catalysis
dc.subject.ddc500 - Science::540 - Chemistry
dc.titleAnion–cation synergistic metal-free catalytic oxidative homocoupling of benzylamines by triazolium iodide salts
dc.typearticle
dspace.entity.typePublication
oaire.citation.endPage7387
oaire.citation.issue37
oaire.citation.startPage7379
oaire.citation.volume18
oairecerif.author.affiliationDepartement für Chemie und Biochemie (DCB)
oairecerif.author.affiliationDepartement für Chemie und Biochemie (DCB)
oairecerif.author.affiliation2#PLACEHOLDER_PARENT_METADATA_VALUE#
oairecerif.author.affiliation2#PLACEHOLDER_PARENT_METADATA_VALUE#
oairecerif.author.affiliation3#PLACEHOLDER_PARENT_METADATA_VALUE#
oairecerif.author.affiliation3#PLACEHOLDER_PARENT_METADATA_VALUE#
oairecerif.author.affiliation4#PLACEHOLDER_PARENT_METADATA_VALUE#
oairecerif.author.affiliation4#PLACEHOLDER_PARENT_METADATA_VALUE#
unibe.contributor.rolecreator
unibe.contributor.rolecreator
unibe.date.licenseChanged2021-02-03 11:22:26
unibe.description.ispublishedpub
unibe.eprints.legacyId151062
unibe.journal.abbrevTitleORG BIOMOL CHEM
unibe.refereedTRUE
unibe.subtype.articlejournal

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